GB868483A - New intermediates in the synthesis of reserpine and their preparation - Google Patents
New intermediates in the synthesis of reserpine and their preparationInfo
- Publication number
- GB868483A GB868483A GB13236/59A GB1323659A GB868483A GB 868483 A GB868483 A GB 868483A GB 13236/59 A GB13236/59 A GB 13236/59A GB 1323659 A GB1323659 A GB 1323659A GB 868483 A GB868483 A GB 868483A
- Authority
- GB
- United Kingdom
- Prior art keywords
- carboxylic acid
- hydroxy
- laevo
- oxo
- hexahydronaphthalene
- 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
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention comprises (a) dextro- and laevo- 5b -hydroxy-8-oxo-1,4,4aa ,5,8, 8aa -hexahydronaphthalene-1b -carboxylic acid, their salts with optically active bases, e.g. quinine, bromine, cinchonine and laevoephedrine, (b) laevo- 1,8,-lactone of 5b -hydroxy-8-oxo-1,4, 4aa ,5,8,8aa - hexahydronaphthalene- 1b - carboxylic acid (c) the laevo- 1,8-lactone of 5b ,8b -dihydroxy- 1,4,4aa ,5,8, 8aa - hexahydronaphthalene-1b -carboxylic acid, (d) the dextrolactone of 8b -hydroxy-2a -methoxy-3b ,5b -epoxy-1,2,3, 4,4aa ,5,8,8aa - octahydronaphthalene- 1b - carboxylic acid, (e) laevo- 3-hydroxy-2a -methoxy-7- oxo- 1,2,3,4,4aa ,7,8, 8aa - octahydronaphthalene-1-carboxylic acid, (f) its laevomethyl ester and (g) its laevomethyl ester 3-acetate, together with processes for their preparation. Compounds (a) are prepared by optical resolution of the corresponding racemate, (b) is formed by lactonisation of the dextro- (a) with sodium acetate and acetic anhydride in methylene chloride, (c) by reduction of (b) with aluminium isopropylate in isopropanol, (d) by treating the dextrolactone of 8b -hydroxy-2a - bromo-3b ,5b -epoxy- 1,2,3,4,4aa , 5,8,8aa - octahydronaphthalene- 1b - carboxylic acid with sodium methoxide in methanol, (e) by reducing laevolactone of 6a -bromo-8b -hydroxy-2a - methoxy-3b ,5b - epoxy-7- oxo-4aa , 8aa - decahydronaphthalene-1b - carboxylic acid with zinc powder in a solvent, (f) by esterification of (e) with diazomethane and (g) by acetylation of (f) with acetic anhydride in a tertiary base. Detailed examples are given.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR868483X | 1956-10-31 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB868483A true GB868483A (en) | 1961-05-17 |
Family
ID=9346158
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB13236/59A Expired GB868483A (en) | 1956-10-31 | 1957-10-30 | New intermediates in the synthesis of reserpine and their preparation |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB868483A (en) |
-
1957
- 1957-10-30 GB GB13236/59A patent/GB868483A/en not_active Expired
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