GB1376123A - Enolates of 9alpha-halo-11-ketosteroids and products prepared therefrom - Google Patents
Enolates of 9alpha-halo-11-ketosteroids and products prepared therefromInfo
- Publication number
- GB1376123A GB1376123A GB5467170A GB5467170A GB1376123A GB 1376123 A GB1376123 A GB 1376123A GB 5467170 A GB5467170 A GB 5467170A GB 5467170 A GB5467170 A GB 5467170A GB 1376123 A GB1376123 A GB 1376123A
- Authority
- GB
- United Kingdom
- Prior art keywords
- enolate
- oxo
- halo
- enol
- converted
- Prior art date
- Legal status (The legal status 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 status listed.)
- Expired
Links
- 238000006243 chemical reaction Methods 0.000 abstract 5
- 238000000034 method Methods 0.000 abstract 4
- -1 enol ester Chemical class 0.000 abstract 3
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical compound [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 abstract 2
- 150000002085 enols Chemical class 0.000 abstract 2
- 229910052744 lithium Inorganic materials 0.000 abstract 2
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 abstract 2
- BHDHELFREODRJK-XRYUJSLGSA-N (8s,9r,10s,13s,14s,17r)-9-fluoro-17-hydroxy-17-(2-hydroxyacetyl)-10,13-dimethyl-2,6,7,8,12,14,15,16-octahydro-1h-cyclopenta[a]phenanthrene-3,11-dione Chemical class O=C1CC[C@]2(C)[C@@]3(F)C(=O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 BHDHELFREODRJK-XRYUJSLGSA-N 0.000 abstract 1
- NOGFHTGYPKWWRX-UHFFFAOYSA-N 2,2,6,6-tetramethyloxan-4-one Chemical compound CC1(C)CC(=O)CC(C)(C)O1 NOGFHTGYPKWWRX-UHFFFAOYSA-N 0.000 abstract 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 238000005837 enolization reaction Methods 0.000 abstract 1
- 239000003880 polar aprotic solvent Substances 0.000 abstract 1
- 125000006239 protecting group Chemical group 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
- 150000003431 steroids Chemical class 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
- C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table compounds of the platinum group
- C07F15/0086—Platinum compounds
- C07F15/0093—Platinum compounds without a metal-carbon linkage
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Steroid Compounds (AREA)
Abstract
1376123 #<SP>11</SP>-Enolates; 12-halosteroids RESEARCH INSTITUTE FOR MEDICINE & CHEMISTRY Inc 15 Nov 1971 [17 Nov 1970] 54671/70 Heading C2U The invention comprises (A) a process for the 11,12-enolization of a 9α-halo-11-oxosteroid having at least one 12-hydrogen atom, by treating it in a polar aprotic medium with a strong base; (B) a solution of a 9α-halosteroid- 11,12-enolate in a polar aprotic solvent; and (C) 9α,12,12-trifluoro-11-oxo and -11-hydroxysteroids. Thus a 9α-halo-11-oxo-12-unsubstituted steroid is converted by process (A) to a Na, K, Li or Mg enolate (the Li enolate being obtainable either directly with Buhi, or by treating an initially obtained Na enolate with LiCl, or by treating a corresponding enol ester with a lithium base). The enolate may be converted to (i) an enol ester by reaction with an acid derivative, e.g. benzoic anhydride; or (ii) an enol silyl ether by reaction, e.g. with Me 3 SiCl; or (iii) a 9α,12-dihalo-11-oxo steroid by reaction with Cl 2 , Br 2 , ClO 3 F or FOCF 3 . The 9α,12-dihalo-11-oxo steroid may be converted to (i) the corresponding 11-ol by reaction with, e.g. NaBH 4 ; or (ii) an enolate by process (A). The enolate may be acidified to give the 12-epimer of the initial 9α,12-dihalo- 11-oxo steroid, or may be converted by methods analogous to those described above to (i) an enol ester; or (ii) an enol silyl ether; or (iii) a 9α-halo-12,12-difluoro-11-oxo steroid. The latter may be reduced to the corresponding 11-ol and any protecting groups (e.g. 3-ketal, 3-enol ether and 17,20;20,21-bismethylenedioxy) removed. In the examples the starting materials for the above conversions are protected derivatives of 9α-fluorocortisone and 9α-fluoro-16α-methylprednisone.
Priority Applications (11)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB5467170A GB1376123A (en) | 1970-11-17 | 1970-11-17 | Enolates of 9alpha-halo-11-ketosteroids and products prepared therefrom |
| IL38143A IL38143A (en) | 1970-11-17 | 1971-11-15 | Process for the preparation of 11,12-enolates of 9alpha-halo-11-keto steroids and of 9alpha,12-dihalo or 9alpha,12,12,12-trihalo 11-keto(or11-hydroxy)steroids |
| AU35753/71A AU458926B2 (en) | 1970-11-17 | 1971-11-16 | Steroid enolates and process forthe preparation thereof |
| CH1663371A CH606104A5 (en) | 1970-11-17 | 1971-11-16 | |
| CA127,749A CA956936A (en) | 1970-11-17 | 1971-11-16 | Processes for the preparation of novel steroid enolates and their use as intermediates |
| FR7140970A FR2114753A5 (en) | 1970-11-17 | 1971-11-16 | |
| DE19712156882 DE2156882A1 (en) | 1970-11-17 | 1971-11-16 | |
| ZA717735A ZA717735B (en) | 1970-11-17 | 1971-11-17 | Novel steroid enolates and processes for their preparation |
| BE775453A BE775453A (en) | 1970-11-17 | 1971-11-17 | PROCESS FOR ENOLIZING STEROIDS AND PRODUCTS |
| NL7115855A NL7115855A (en) | 1970-11-17 | 1971-11-17 | |
| AR239082A AR193361A1 (en) | 1970-11-17 | 1971-11-17 | A PROCEDURE FOR THE PREPARATION OF A STEROID ENOLATE |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB5467170A GB1376123A (en) | 1970-11-17 | 1970-11-17 | Enolates of 9alpha-halo-11-ketosteroids and products prepared therefrom |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1376123A true GB1376123A (en) | 1974-12-04 |
Family
ID=10471736
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB5467170A Expired GB1376123A (en) | 1970-11-17 | 1970-11-17 | Enolates of 9alpha-halo-11-ketosteroids and products prepared therefrom |
Country Status (11)
| Country | Link |
|---|---|
| AR (1) | AR193361A1 (en) |
| AU (1) | AU458926B2 (en) |
| BE (1) | BE775453A (en) |
| CA (1) | CA956936A (en) |
| CH (1) | CH606104A5 (en) |
| DE (1) | DE2156882A1 (en) |
| FR (1) | FR2114753A5 (en) |
| GB (1) | GB1376123A (en) |
| IL (1) | IL38143A (en) |
| NL (1) | NL7115855A (en) |
| ZA (1) | ZA717735B (en) |
-
1970
- 1970-11-17 GB GB5467170A patent/GB1376123A/en not_active Expired
-
1971
- 1971-11-15 IL IL38143A patent/IL38143A/en unknown
- 1971-11-16 FR FR7140970A patent/FR2114753A5/fr not_active Expired
- 1971-11-16 CA CA127,749A patent/CA956936A/en not_active Expired
- 1971-11-16 DE DE19712156882 patent/DE2156882A1/de active Pending
- 1971-11-16 CH CH1663371A patent/CH606104A5/xx not_active IP Right Cessation
- 1971-11-16 AU AU35753/71A patent/AU458926B2/en not_active Expired
- 1971-11-17 ZA ZA717735A patent/ZA717735B/en unknown
- 1971-11-17 NL NL7115855A patent/NL7115855A/xx unknown
- 1971-11-17 BE BE775453A patent/BE775453A/en unknown
- 1971-11-17 AR AR239082A patent/AR193361A1/en active
Also Published As
| Publication number | Publication date |
|---|---|
| AR193361A1 (en) | 1973-04-23 |
| AU458926B2 (en) | 1975-02-24 |
| CA956936A (en) | 1974-10-29 |
| FR2114753A5 (en) | 1972-06-30 |
| IL38143A (en) | 1977-08-31 |
| DE2156882A1 (en) | 1972-05-25 |
| ZA717735B (en) | 1972-11-29 |
| CH606104A5 (en) | 1978-10-13 |
| NL7115855A (en) | 1972-05-19 |
| AU3575371A (en) | 1973-05-24 |
| BE775453A (en) | 1972-05-17 |
| IL38143A0 (en) | 1972-01-27 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| PLNP | Patent lapsed through nonpayment of renewal fees |