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, followed by reacting the obtained 3,5-dienol ether in a dimethylformamide medium with phosphorus oxychloride at 5-10°C and treating the reaction mixture with aqueous potassium carbonate solution containing sodium chloride, and reacting the obtained unsaturated aldehyde with sodium borohydride in a methanol medium at room temperature, followed by treating the reaction mixture with concentrated hydrochloric acid.
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 |
---|---|---|---|
METHOD OF PRODUCING 6-METHYLENO-16α,17α-CYCLOHEXANOPREGN-4-ENE-3,20-DIONE | 2014 |
|
RU2566366C1 |
METHOD OF OBTAINING 6α-METHYLHYDROCORTISONE OR ITS 11β-ALKANOYLOXY-DERIVATIVES (VERSIONS), METHOD OF OBTAINING 6α-METHYLPREDNISOLONE OR ITS 11β-ALKANOYLOXY-DERIVATIVES USING OBTAINED 6α-METHYLHYDROCORTISONE OR ITS 11β-ALKANOYLOXY-DERIVATIVES | 2006 |
|
RU2337918C9 |
METHOD OF PRODUCING 16α,17α-CYCLOHEXANO-5α,6α-EPOXYPREGN-3β-OL-20-ONE ACETATE | 2011 |
|
RU2480477C1 |
METHOD OF PREPARATION 6α-METHYLHYDROCORTISONE OR ESTERS THEREOF FROM HYDROCORTISONE 21-ACETATE | 2017 |
|
RU2663484C1 |
METHOD OF OBTAINING 11BETA, 17 ALPHA, 21-TRIHYDROXY-16ALPHA-METHYL-9ALPHA-FLUOROPREGNA-1,4-DIENE-3,20-DIONE (DEXAMETHAZONE) FROM PHYTOSTEROL | 2013 |
|
RU2532902C1 |
METHOD FOR OBTAINING 6-DEHYDRO-6-METHYLHYDROCORTISONE OR ESTER THEREOF FROM HYDROCORTISONE 21-ACETATE | 2017 |
|
RU2663893C1 |
METHOD FOR PREPARING 6α-METHYLHYDROCORTISONE | 2006 |
|
RU2297423C1 |
METHOD FOR PRODUCING 6-METHYLENEHYDROCORTISONE OR ESTERS THEREOF FROM HYDROCORTISONE 21-ACETATE | 2017 |
|
RU2664101C1 |
4-HETERO-16α, 17α-CYCLOHEXANOPREGNANES | 2009 |
|
RU2426737C1 |
METHOD OF PRODUCING 3β-ACETOXY-17α-HYDROPEROXY-16α-METHYLPREGNANES FROM Δ-20-KETOSTEROIDS AND METHOD OF PRODUCING 3β-ACETOXY-17α-HYDROXY-16α-METHYLPREGNANES USING 3β-ACETOXY-17α-HYDROPEROXY-16α-METHYLPREGNANES | 2009 |
|
RU2418805C1 |
Authors
Dates
2015-10-27—Published
2014-12-05—Filed