GB906138A - Improvements in or relating to 20ª--yohimbanes - Google Patents

Improvements in or relating to 20ª--yohimbanes

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Publication number
GB906138A
GB906138A GB2713859A GB2713859A GB906138A GB 906138 A GB906138 A GB 906138A GB 2713859 A GB2713859 A GB 2713859A GB 2713859 A GB2713859 A GB 2713859A GB 906138 A GB906138 A GB 906138A
Authority
GB
United Kingdom
Prior art keywords
ethyl
dimethoxy
methoxycarbonyl
acetoxy
hydroxy
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
GB2713859A
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.)
Sanofi Aventis France
Original Assignee
Roussel Uclaf SA
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 Roussel Uclaf SA filed Critical Roussel Uclaf SA
Publication of GB906138A publication Critical patent/GB906138A/en
Expired legal-status Critical Current

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  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

The invention comprises 6-ethyl reserpine and the following intermediates used in its synthesis:- the quaternary base of the lactone of 6-ethyl-11, 17a -dimethoxy-16b -carboxy-18b -hydroxy-D 3-20a -yohimbene, (I), the lactone of 6 - ethyl - 11,17a - dimethoxy-16b -carboxy-18b -hydroxy-3a ,20a -yohimbene, (II), its 3b -epimer, and 6 - ethyl - 11,17a -dimethoxy-16b -methoxycarbonyl-18b -hydroxy-3b , 20a -yohimbane, together with a process for the preparation of a 6-ethyl reserpine by condensing 2-(61-methoxy-31-indolyl)-1-butylamine with dextro-1b - carboxymethyl - 2b - methoxycarbonyl-3a -methoxy - 4b - acetoxy-6b -formyl-cyclohexane, reducing the resulting 6-ethyl-11,17a -dimethoxy-16b - methoxycarbonyl - 18b - acetoxy-2,3-3,4-diseco-D 4(21)-20a -yohimbene-3-oic acid with an alkali metal hydride, cyclizing by dehydration the resulting 6 - ethyl-11,17a -dimethoxy-16b -methoxycarbonyl - 18b - acetoxy-2,3-3,4-diseco-20a -yohimbane-3-oic acid to give 6-ethyl-11,17a -dimethoxy - 16b -methoxycarbonyl-18b -acetoxy-2,3-seco-3-oxo-20a -yohimbane, saponifying and lactonising the 16b -carboxy-18b -hydroxy product and cyclizing the lactone by means of a dehydrating agent to give I, which is reduced with a metal hydride reducing agent, the product II epimerised with acid and subjected to methanolysis and finally trimethoxybenzoylation to give 6-ethyl reserpine. Specifications 868,479, 888,411 and 899,549 are referred to.
GB2713859A 1958-08-08 1959-08-07 Improvements in or relating to 20ª--yohimbanes Expired GB906138A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
FR772125 1958-08-08

Publications (1)

Publication Number Publication Date
GB906138A true GB906138A (en) 1962-09-19

Family

ID=8707213

Family Applications (1)

Application Number Title Priority Date Filing Date
GB2713859A Expired GB906138A (en) 1958-08-08 1959-08-07 Improvements in or relating to 20ª--yohimbanes

Country Status (2)

Country Link
CH (1) CH387056A (en)
GB (1) GB906138A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN112010773A (en) * 2020-08-18 2020-12-01 深圳市辛骏翔科技有限公司 Dehydrating agent and preparation method thereof, and hydrocarbon water cutting agent and preparation method thereof

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN112010773A (en) * 2020-08-18 2020-12-01 深圳市辛骏翔科技有限公司 Dehydrating agent and preparation method thereof, and hydrocarbon water cutting agent and preparation method thereof

Also Published As

Publication number Publication date
CH387056A (en) 1965-01-31

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