GB799272A - Production of intermediates for the synthesis of reserpine and analogous compounds - Google Patents

Production of intermediates for the synthesis of reserpine and analogous compounds

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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
Application number
GB32598/57A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Research Corp
Original Assignee
Research Corp
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.)
Filing date
Publication date
Application filed by Research Corp filed Critical Research Corp
Publication of GB799272A publication Critical patent/GB799272A/en
Expired legal-status Critical Current

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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.
GB32598/57A 1956-05-03 1957-05-03 Production of intermediates for the synthesis of reserpine and analogous compounds Expired GB799272A (en)

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)

* Cited by examiner, † Cited by third party
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

Cited By (1)

* Cited by examiner, † Cited by third party
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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