FIELD: chemistry.
SUBSTANCE: invention relates to a method of producing 6-methyleno-16α,17α-cyclohexanopregn-4-ene-3,20-dione of formula (I) which is an immediate precursor in synthesis of high-efficiency progestin - 6α-methyl-16α,17α-cyclohexano-progesterone. The method includes reacting 16α,17α-cyclohexanopregn-4-ene-3,20-dione with trimethyl orthoformate in a methanol medium or with triethyl orthoformate in an ethanol medium in the presence of para-toluene sulphonic acid at room temperature, and treating the obtained reaction mass containing the corresponding 3,5-dienol ether with N-methylaniline and 37% aqueous formaldehyde solution, holding the reaction mixture at 35-40°C, pouring into water cooled to 8-10°C, which contains sodium hydroxide, followed by extraction of the obtained isomeric mixture of 6α- and 6β-isomers of an (N-methyl-N-phenylaminomethyl)-derivative and treatment thereof with concentrated hydrochloric acid at room temperature.
EFFECT: effective protection of an authentic electronic image, high output of the end product, conducting the process in mild conditions, easy extraction of intermediate and end products.
2 ex
Title | Year | Author | Number |
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METHOD OF PRODUCING 6-METHYLENO-16α,17α-CYCLOHEXANOPREGN-4-ENE-3,20-DIONE | 2014 |
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METHOD FOR OBTAINING 6-DEHYDRO-6-METHYLHYDROCORTISONE OR ESTER THEREOF FROM HYDROCORTISONE 21-ACETATE | 2017 |
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N-SUBSTITUTED DERIVATIVES OF 6α-PIPERAZINOMETHYLANDROOST-4-EN-3,17-DIONE, HAVING ANTIMICROBIAL ACTIVITY, AND THEIR PRODUCTION METHOD | 2023 |
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METHOD OF PRODUCING 6-METHYLENEANDROST-4-ENE-3,17-DIONE FROM ANDROST-4-ENE-3,17-DIONE, METHOD OF PRODUCING 6-METHYLENEANDROST-1,4-DIENE-3,17-DIONE (EXEMESTANE) USING OBTAINED 6-METHYLENEANDROST-4-ENE-3,17-DIONE | 2010 |
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RU2425052C1 |
METHOD FOR PREPARING 6α-METHYLHYDROCORTISONE | 2006 |
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Authors
Dates
2015-10-27—Published
2014-12-05—Filed