CS210692B2 - Manufacturing process of 3-benzyl-3-azabicyclo(l3.1.0)phexane - Google Patents

Manufacturing process of 3-benzyl-3-azabicyclo(l3.1.0)phexane Download PDF

Info

Publication number: CS210692B2
Authority: CS; Czechoslovakia
Prior art keywords: azabicyclo; hexane; benzyl; mixture; liters
Prior art date: 1978-07-06

Application number

CS794719A

Other languages

Czech (cs)

English (en)

Inventor

Willy D Kollmeyer

Original Assignee

Shell Int Research

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1978-07-06

Filing date

1979-07-04

Publication date

1982-01-29

1979-07-04 Application filed by Shell Int Research filed Critical Shell Int Research

1982-01-29 Publication of CS210692B2 publication Critical patent/CS210692B2/cs

Links

238000004519 manufacturing process Methods 0.000 title 1
OQEHGZOASMRNJW-UHFFFAOYSA-N 3-benzyl-3-azabicyclo[3.1.0]hexane Chemical compound C1C2CC2CN1CC1=CC=CC=C1 OQEHGZOASMRNJW-UHFFFAOYSA-N 0.000 claims abstract description 13
JEISWFNRNZRSHM-UHFFFAOYSA-N 3-benzyl-3-azabicyclo[3.1.0]hexane-2,4-dione Chemical compound O=C1C2CC2C(=O)N1CC1=CC=CC=C1 JEISWFNRNZRSHM-UHFFFAOYSA-N 0.000 claims abstract description 11
239000003638 chemical reducing agent Substances 0.000 claims abstract description 9
238000002360 preparation method Methods 0.000 claims abstract description 7
AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical compound [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 claims abstract description 4
238000006243 chemical reaction Methods 0.000 claims description 22
238000000034 method Methods 0.000 claims description 9
-1 lithium aluminum hydride Chemical group 0.000 claims description 5
JEDZLBFUGJTJGQ-UHFFFAOYSA-N [Na].COCCO[AlH]OCCOC Chemical compound [Na].COCCO[AlH]OCCOC JEDZLBFUGJTJGQ-UHFFFAOYSA-N 0.000 claims description 4
239000012280 lithium aluminium hydride Substances 0.000 claims description 3
DNEHKUCSURWDGO-UHFFFAOYSA-N aluminum sodium Chemical compound [Na].[Al] DNEHKUCSURWDGO-UHFFFAOYSA-N 0.000 claims description 2
VSKBCRUQHHGABO-UHFFFAOYSA-N [Al].[H][H].[H][H].[H][H] Chemical compound [Al].[H][H].[H][H].[H][H] VSKBCRUQHHGABO-UHFFFAOYSA-N 0.000 claims 1
150000001875 compounds Chemical class 0.000 abstract description 7
230000004071 biological effect Effects 0.000 abstract description 2
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 abstract description 2
JBDOTWVUXVXVDR-UHFFFAOYSA-N 3-azoniabicyclo[3.1.0]hexane-2-carboxylate Chemical compound OC(=O)C1NCC2CC12 JBDOTWVUXVXVDR-UHFFFAOYSA-N 0.000 abstract 1
229910000091 aluminium hydride Inorganic materials 0.000 abstract 1
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 51
239000000203 mixture Substances 0.000 description 28
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 21
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 21
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 15
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 14
239000002904 solvent Substances 0.000 description 12
239000000243 solution Substances 0.000 description 11
239000002253 acid Substances 0.000 description 10
238000009835 boiling Methods 0.000 description 9
239000000047 product Substances 0.000 description 9
239000011541 reaction mixture Substances 0.000 description 9
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 8
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 8
238000010438 heat treatment Methods 0.000 description 8
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 7
239000003054 catalyst Substances 0.000 description 7
238000001816 cooling Methods 0.000 description 7
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
150000008064 anhydrides Chemical class 0.000 description 6
QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
HGWUUOXXAIISDB-UHFFFAOYSA-N 3-azabicyclo[3.1.0]hexane Chemical compound C1NCC2CC21 HGWUUOXXAIISDB-UHFFFAOYSA-N 0.000 description 5
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 5
238000004821 distillation Methods 0.000 description 5
239000001257 hydrogen Substances 0.000 description 5
229910052739 hydrogen Inorganic materials 0.000 description 5
239000007788 liquid Substances 0.000 description 5
238000003756 stirring Methods 0.000 description 5
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
239000012043 crude product Substances 0.000 description 4
150000002148 esters Chemical class 0.000 description 4
239000010410 layer Substances 0.000 description 4
238000002844 melting Methods 0.000 description 4
230000008018 melting Effects 0.000 description 4
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
229910052757 nitrogen Inorganic materials 0.000 description 4
229910052763 palladium Inorganic materials 0.000 description 4
238000010992 reflux Methods 0.000 description 4
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
239000006227 byproduct Substances 0.000 description 3
239000007789 gas Substances 0.000 description 3
229930195733 hydrocarbon Natural products 0.000 description 3
150000002430 hydrocarbons Chemical class 0.000 description 3
229910052943 magnesium sulfate Inorganic materials 0.000 description 3
235000019341 magnesium sulphate Nutrition 0.000 description 3
239000012071 phase Substances 0.000 description 3
150000003839 salts Chemical class 0.000 description 3
239000007858 starting material Substances 0.000 description 3
239000000126 substance Substances 0.000 description 3
ZRMYHUFDVLRYPN-UHFFFAOYSA-N 3-oxabicyclo[3.1.0]hexane-2,4-dione Chemical compound O=C1OC(=O)C2CC12 ZRMYHUFDVLRYPN-UHFFFAOYSA-N 0.000 description 2
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 2
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 2
QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
229960000583 acetic acid Drugs 0.000 description 2
239000002518 antifoaming agent Substances 0.000 description 2
238000009903 catalytic hydrogenation reaction Methods 0.000 description 2
125000004122 cyclic group Chemical group 0.000 description 2
150000005690 diesters Chemical class 0.000 description 2
SXLDHZFJMXLFJU-RNFRBKRXSA-N diethyl (1r,2r)-cyclopropane-1,2-dicarboxylate Chemical compound CCOC(=O)[C@@H]1C[C@H]1C(=O)OCC SXLDHZFJMXLFJU-RNFRBKRXSA-N 0.000 description 2
SXLDHZFJMXLFJU-KNVOCYPGSA-N diethyl (1r,2s)-cyclopropane-1,2-dicarboxylate Chemical compound CCOC(=O)[C@H]1C[C@H]1C(=O)OCC SXLDHZFJMXLFJU-KNVOCYPGSA-N 0.000 description 2
239000006185 dispersion Substances 0.000 description 2
VEUUMBGHMNQHGO-UHFFFAOYSA-N ethyl chloroacetate Chemical compound CCOC(=O)CCl VEUUMBGHMNQHGO-UHFFFAOYSA-N 0.000 description 2
239000000284 extract Substances 0.000 description 2
238000001914 filtration Methods 0.000 description 2
235000019253 formic acid Nutrition 0.000 description 2
239000011521 glass Substances 0.000 description 2
238000007327 hydrogenolysis reaction Methods 0.000 description 2
239000000543 intermediate Substances 0.000 description 2
239000002480 mineral oil Substances 0.000 description 2
235000010446 mineral oil Nutrition 0.000 description 2
238000002156 mixing Methods 0.000 description 2
239000012299 nitrogen atmosphere Substances 0.000 description 2
239000012044 organic layer Substances 0.000 description 2
PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 2
239000000376 reactant Substances 0.000 description 2
239000012419 sodium bis(2-methoxyethoxy)aluminum hydride Substances 0.000 description 2
239000012312 sodium hydride Substances 0.000 description 2
229910000104 sodium hydride Inorganic materials 0.000 description 2
229910052938 sodium sulfate Inorganic materials 0.000 description 2
235000011152 sodium sulphate Nutrition 0.000 description 2
239000007787 solid Substances 0.000 description 2
239000000725 suspension Substances 0.000 description 2
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 2
239000008096 xylene Substances 0.000 description 2
RLWFMZKPPHHHCB-WSOKHJQSSA-N (1r,2s)-cyclopropane-1,2-dicarboxylic acid Chemical compound OC(=O)[C@H]1C[C@H]1C(O)=O RLWFMZKPPHHHCB-WSOKHJQSSA-N 0.000 description 1
ZRMYHUFDVLRYPN-WSOKHJQSSA-N (1s,5r)-3-oxabicyclo[3.1.0]hexane-2,4-dione Chemical compound O=C1OC(=O)[C@@H]2C[C@H]12 ZRMYHUFDVLRYPN-WSOKHJQSSA-N 0.000 description 1
DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 description 1
WJXYUEOVOQGJGV-UHFFFAOYSA-N 3-azabicyclo[3.1.0]hexane;hydrochloride Chemical compound Cl.C1NCC2CC21 WJXYUEOVOQGJGV-UHFFFAOYSA-N 0.000 description 1
LEQKPQQOCKLKHK-UHFFFAOYSA-N 3-cyclohexylpiperidine Chemical group C1CCCCC1C1CNCCC1 LEQKPQQOCKLKHK-UHFFFAOYSA-N 0.000 description 1
QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 1
239000004215 Carbon black (E152) Substances 0.000 description 1
XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 1
239000005909 Kieselgur Substances 0.000 description 1
238000005481 NMR spectroscopy Methods 0.000 description 1
239000004280 Sodium formate Substances 0.000 description 1
150000008065 acid anhydrides Chemical class 0.000 description 1
230000002411 adverse Effects 0.000 description 1
238000007605 air drying Methods 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
239000000538 analytical sample Substances 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
238000010533 azeotropic distillation Methods 0.000 description 1
239000002585 base Substances 0.000 description 1
239000001569 carbon dioxide Substances 0.000 description 1
229910002092 carbon dioxide Inorganic materials 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
239000008139 complexing agent Substances 0.000 description 1
RLWFMZKPPHHHCB-UHFFFAOYSA-N cyclopropane-1,2-dicarboxylate;hydron Chemical compound OC(=O)C1CC1C(O)=O RLWFMZKPPHHHCB-UHFFFAOYSA-N 0.000 description 1
YMGUBTXCNDTFJI-UHFFFAOYSA-N cyclopropanecarboxylic acid Chemical compound OC(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-N 0.000 description 1
230000007547 defect Effects 0.000 description 1
230000018044 dehydration Effects 0.000 description 1
238000006297 dehydration reaction Methods 0.000 description 1
YGEGVBWONVKDHX-UHFFFAOYSA-N diethyl 2-cyano-3-methylbutanedioate Chemical class CCOC(=O)C(C)C(C#N)C(=O)OCC YGEGVBWONVKDHX-UHFFFAOYSA-N 0.000 description 1
SXLDHZFJMXLFJU-UHFFFAOYSA-N diethyl cyclopropane-1,2-dicarboxylate Chemical compound CCOC(=O)C1CC1C(=O)OCC SXLDHZFJMXLFJU-UHFFFAOYSA-N 0.000 description 1
125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
230000000694 effects Effects 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
238000011049 filling Methods 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 1
239000012362 glacial acetic acid Substances 0.000 description 1
NDOGLIPWGGRQCO-UHFFFAOYSA-N hexane-2,4-dione Chemical compound CCC(=O)CC(C)=O NDOGLIPWGGRQCO-UHFFFAOYSA-N 0.000 description 1
150000004678 hydrides Chemical class 0.000 description 1
150000002431 hydrogen Chemical class 0.000 description 1
238000011065 in-situ storage Methods 0.000 description 1
239000003999 initiator Substances 0.000 description 1
230000000977 initiatory effect Effects 0.000 description 1
238000002955 isolation Methods 0.000 description 1
239000000463 material Substances 0.000 description 1
229910052987 metal hydride Inorganic materials 0.000 description 1
150000004681 metal hydrides Chemical class 0.000 description 1
229910000510 noble metal Inorganic materials 0.000 description 1
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
239000003921 oil Substances 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
238000005191 phase separation Methods 0.000 description 1
229920000642 polymer Polymers 0.000 description 1
238000007363 ring formation reaction Methods 0.000 description 1
238000002390 rotary evaporation Methods 0.000 description 1
238000007127 saponification reaction Methods 0.000 description 1
239000002002 slurry Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
HLBBKKJFGFRGMU-UHFFFAOYSA-M sodium formate Chemical compound [Na+].[O-]C=O HLBBKKJFGFRGMU-UHFFFAOYSA-M 0.000 description 1
235000019254 sodium formate Nutrition 0.000 description 1
230000003595 spectral effect Effects 0.000 description 1
229910001220 stainless steel Inorganic materials 0.000 description 1
239000010935 stainless steel Substances 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
238000001665 trituration Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/52—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring condensed with a ring other than six-membered
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/09—Preparation of carboxylic acids or their salts, halides or anhydrides from carboxylic acid esters or lactones
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/54—Preparation of carboxylic acid anhydrides
- C07C51/56—Preparation of carboxylic acid anhydrides from organic acids, their salts, their esters or their halides, e.g. by carboxylation

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Engineering & Computer Science (AREA)
Oil, Petroleum & Natural Gas (AREA)
Indole Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

CS794719A 1978-07-06 1979-07-04 Manufacturing process of 3-benzyl-3-azabicyclo(l3.1.0)phexane CS210692B2 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US05/922,407 US4183857A (en)	1978-07-06	1978-07-06	3-Benzyl-3-azabicyclo(3.1.0)hexane-2,4-dione

Publications (1)

Publication Number	Publication Date
CS210692B2 true CS210692B2 (en)	1982-01-29

Family

ID=25446984

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CS794719A CS210692B2 (en)	1978-07-06	1979-07-04	Manufacturing process of 3-benzyl-3-azabicyclo(l3.1.0)phexane

Country Status (15)

Country	Link
US (1)	US4183857A (pt)
EP (1)	EP0007128B1 (pt)
JP (1)	JPS5511587A (pt)
AU (1)	AU527833B2 (pt)
BR (1)	BR7904218A (pt)
CA (1)	CA1116612A (pt)
CS (1)	CS210692B2 (pt)
DD (1)	DD144768A5 (pt)
DE (1)	DE2964802D1 (pt)
DK (1)	DK240979A (pt)
ES (1)	ES482177A1 (pt)
IL (1)	IL57718A0 (pt)
PL (1)	PL116900B1 (pt)
SU (1)	SU969158A3 (pt)
ZA (1)	ZA793334B (pt)

Families Citing this family (14)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CA1116617A (en) *	1978-12-14	1982-01-19	Janet A. Day	Esters of 2-carboxy-3-azabicyclo¬3.1.0\|hex-2-ene
US5256791A (en) *	1992-03-02	1993-10-26	Pfizer Inc.	Preparation of intermediates in the synthesis of quinoline antibiotics
GB9620049D0 (en) *	1996-09-26	1996-11-13	Hayles J R	Repellent formulations
US6395767B2 (en)	2000-03-10	2002-05-28	Bristol-Myers Squibb Company	Cyclopropyl-fused pyrrolidine-based inhibitors of dipeptidyl peptidase IV and method
DE60226906D1 (de) *	2002-07-31	2008-07-10	Ranbaxy Lab Ltd	3,6-disubstituierte azabicyclo ä3.1.0ühexanderivate, die sich als muscarinrezeptorantagonisten eignen
AU2002321711A1 (en) *	2002-08-09	2004-02-25	Ranbaxy Laboratories Limited	3,6-disubstituted azabicyclo (3.1.0) hexane derivatives useful as muscarinic receptor antagonist
US6875784B2 (en) *	2002-10-09	2005-04-05	Pharmacia & Upjohn Company	Antimibicrobial [3.1.0.] bicyclic oxazolidinone derivatives
ATE466007T1 (de) *	2005-11-30	2010-05-15	Hoffmann La Roche	5-substituierte indol-2-carbonsäureamidderivate
CA2634397A1 (en) *	2005-12-22	2007-07-05	Schering Corporation	Process for the preparation of 6,6-dimethyl-3-azabicyclo[3.1.0\|-hexane compounds and enantiomeric salts thereof
US8158807B2 (en) *	2006-12-20	2012-04-17	Schering Corporation	Process for the preparation of 6,6-dimethyl-3-azabicyclo-[3.1.0]-hexane compounds utilizing bisulfite intermediate
CN102131813B (zh)	2008-06-24	2014-07-30	科德克希思公司	用于制备基本上立体异构纯的稠合二环脯氨酸化合物的生物催化方法
CN102432525A (zh) *	2011-10-20	2012-05-02	苏州康润医药有限公司	3-苄基-3-氮杂二环[2,1,0]己烷的实用合成方法
CN108341766B (zh) *	2017-01-24	2020-08-14	南京药石科技股份有限公司	一种3-氮杂双环[3.1.0]己烷盐酸盐的制备方法
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1978
- 1978-07-06 US US05/922,407 patent/US4183857A/en not_active Expired - Lifetime
1979
- 1979-06-08 DK DK240979A patent/DK240979A/da not_active Application Discontinuation
- 1979-06-14 CA CA000329751A patent/CA1116612A/en not_active Expired
- 1979-06-27 EP EP79200347A patent/EP0007128B1/en not_active Expired
- 1979-06-27 DE DE7979200347T patent/DE2964802D1/de not_active Expired
- 1979-07-04 ES ES482177A patent/ES482177A1/es not_active Expired
- 1979-07-04 PL PL1979216848A patent/PL116900B1/pl unknown
- 1979-07-04 ZA ZA793334A patent/ZA793334B/xx unknown
- 1979-07-04 JP JP8404979A patent/JPS5511587A/ja active Pending
- 1979-07-04 SU SU792783601A patent/SU969158A3/ru active
- 1979-07-04 CS CS794719A patent/CS210692B2/cs unknown
- 1979-07-04 IL IL57718A patent/IL57718A0/xx unknown
- 1979-07-04 BR BR7904218A patent/BR7904218A/pt unknown
- 1979-07-04 AU AU48636/79A patent/AU527833B2/en not_active Ceased
- 1979-07-04 DD DD79214104A patent/DD144768A5/de unknown

Also Published As

Publication number	Publication date
AU527833B2 (en)	1983-03-24
IL57718A0 (en)	1979-11-30
DE2964802D1 (en)	1983-03-24
DD144768A5 (de)	1980-11-05
ES482177A1 (es)	1980-06-16
EP0007128B1 (en)	1983-02-16
ZA793334B (en)	1980-06-25
SU969158A3 (ru)	1982-10-23
US4183857A (en)	1980-01-15
EP0007128A1 (en)	1980-01-23
CA1116612A (en)	1982-01-19
BR7904218A (pt)	1981-01-05
PL216848A1 (pt)	1980-03-24
DK240979A (da)	1980-01-07
AU4863679A (en)	1980-01-10
PL116900B1 (en)	1981-07-31
JPS5511587A (en)	1980-01-26

Publication	Publication Date	Title
CS210692B2 (en)	1982-01-29	Manufacturing process of 3-benzyl-3-azabicyclo(l3.1.0)phexane
JP2963048B2 (ja)	1999-10-12	９，１０−エンドエタノ−９，１０−ジハイドロアントラセン−１１，１１−ジカルボン酸のモノエステルまたはジエステルの合成方法、この合成方法により得られる新規なモノエステルまたはジエステル、及びこれらの、均整または不整メチリデンマロネートの合成への応用
JPH1192423A (ja)	1999-04-06	トリフルオロ酢酸及びクロロジフルオロ酢酸のメチルエステル又はエチルエステルの製造方法
KR20180117656A (ko)	2018-10-29	테르피넨-4-올의 제조 방법
JPS61286351A (ja)	1986-12-16	シクロプロピルアミンの製造方法
SU1736334A3 (ru)	1992-05-23	Способ получени алкиланилинофумарата
EP0169602B1 (en)	1989-03-01	Preparation of n-substituted azetidine 3-carboxylic acid derivatives
US2931805A (en)	1960-04-05	Spiro [bicyclo [2. 2. 1] heptane-2, 2'-alkylenimines]
EP0379063B1 (en)	1997-12-10	Process for preparing (trans)-4-substituted-DL-proline derivatives
CA1127159A (en)	1982-07-06	Derivatives of 3-azabicyclo(3.1.0)hexane and processes for their preparation
SU1407396A3 (ru)	1988-06-30	Способ получени 8-метокси-4,8-диметил-1-(4-изопропилфенил)-нонана (его варианты)
JP4540197B2 (ja)	2010-09-08	（ｅ）−３−メチル−２−シクロペンタデセノンの製造法
EP0008813B1 (en)	1982-12-01	Processes for the preparation of 3-azabicyclo(3.1.0)hexane derivatives
JPH05201950A (ja)	1993-08-10	Ｎ−（ヒドロキシアルキル）−カルバミン酸アルキルの製法
JPH0417939B2 (pt)	1992-03-26
JPH0250101B2 (pt)	1990-11-01
EP0366149A1 (en)	1990-05-02	Improved process for the synthesis of 3-chloro-2,4,5-trifluorobenzoic acid
JPH0148255B2 (pt)	1989-10-18
JP2683809B2 (ja)	1997-12-03	１−ベンジル−３−ベンジルアミノピロリジン類の製造法
SU1473708A3 (ru)	1989-04-15	Способ получени сложных эфиров тиолкарбаминовой кислоты (его варианты)
JP3584989B2 (ja)	2004-11-04	キラルな亜鉛化合物
GB1578191A (en)	1980-11-05	2,5 - dimenthyl - 3-carbalkoxy - tetrahydrofuren - 4 - ones and their manufacture
JPH0563460B2 (pt)	1993-09-10
DE3235399A1 (de)	1984-03-29	Verfahren zur herstellung von 7-oxabicyclo(2,2,1)hept-5-en-derivaten
SU958411A1 (ru)	1982-09-15	Способ получени @ , @ -разветвленных @ -кетоэфиров