GB799272A - Production of intermediates for the synthesis of reserpine and analogous compounds - Google Patents
Production of intermediates for the synthesis of reserpine and analogous compoundsInfo
- Publication number
- GB799272A GB799272A GB32598/57A GB3259857A GB799272A GB 799272 A GB799272 A GB 799272A GB 32598/57 A GB32598/57 A GB 32598/57A GB 3259857 A GB3259857 A GB 3259857A GB 799272 A GB799272 A GB 799272A
- Authority
- GB
- United Kingdom
- Prior art keywords
- lactone
- acid
- reserpine
- intermediates
- synthesis
- 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
Abstract
The invention comprises (1) isoreserpic acid lactone of the formula: <FORM:0799272/IV (b)/1> and (2) the isomerization (to reserpic acid lactone series) by heating with an acid the above compound or analogues substituted in the benzene ring by (R11O)n, where R11 is C1-C4 alkyl or benzyl and n is 0 or 1. Suitable acids are acetic and trialkylacetic. The process forms a link in the synthesis of reserpine and its analogues, the intermediates being described in Specifications 799,269, 799,270 and 799,271. The lactone: <FORM:0799272/IV (b)/2> obtained as in Specification 799,271 (R = methyl, R1 = acetyl) is ring-closed with phosphorus oxychloride to yield: <FORM:0799272/IV (b)/3> which is then reduced with sodium borohydride to methyl O-acetyl-isoreserpate. After resolution with di-p-toluyl-l-tartaric acid the product is hydrolysed to isoreserpic acid (hydrochloride) from which the lactone is obtained by treatment with dicyclohexyl-carbodiimide. The lactone is then isomerized to reserpic acid lactone which may be converted into reserpine. Examples are given of the various steps. It is stated that the resolution may be effected at an earlier stage.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US799272XA | 1956-05-03 | 1956-05-03 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB799272A true GB799272A (en) | 1958-08-06 |
Family
ID=22153689
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB32598/57A Expired GB799272A (en) | 1956-05-03 | 1957-05-03 | Production of intermediates for the synthesis of reserpine and analogous compounds |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB799272A (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE1137442B (en) * | 1958-10-31 | 1962-10-04 | Chimiotherapie Lab Franc | Process for the preparation of 11-dimethylamonideserpidine |
-
1957
- 1957-05-03 GB GB32598/57A patent/GB799272A/en not_active Expired
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE1137442B (en) * | 1958-10-31 | 1962-10-04 | Chimiotherapie Lab Franc | Process for the preparation of 11-dimethylamonideserpidine |
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