Method for synthesizing finasteride

A technology of finasteride and androsteroid, applied in the field of compound synthesis, can solve the problems of high synthesis cost, low reaction yield, expensive raw material and the like

Inactive Publication Date: 2010-10-20
SHANGHAI INST OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

But there are problems such as expensive raw materials, high synthesis cost, low reaction yield (total yield is only 8.7%)

Method used

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  • Method for synthesizing finasteride
  • Method for synthesizing finasteride

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Embodiment 1

[0041] A kind of synthetic method of finasteride, its technical synthetic route schematic diagram is shown in figure 1 .

[0042] A synthetic method for finasteride, comprising the steps of:

[0043] (1), the synthesis of 3-carbonyl-4-androstene-17β-carboxylic acid

[0044] Progesterone (31.5 g, 100.0 mmol) was dissolved in dioxane (200 mL). At low temperature, top up with Br 2(15.78 g, 98.6 mmol) and 15% sodium hydroxide solution (40 mL). After dropping, react for 6 hours. Pour into ice water (70 mL), extract the aqueous layer with ethyl acetate (40 mL×3), combine the organic phases, wash with appropriate amount of saturated sodium bicarbonate solution and saturated sodium chloride solution, and dry over anhydrous sodium sulfate. The solvent was evaporated to dryness under reduced pressure, and the residue was recrystallized with ethyl acetate to obtain white crystal 3-carbonyl-4-androstene-17β-carboxylic acid (27.80 g, yield 88%), mp 246~247 ° C (document mp 245~248℃);...

Embodiment 2

[0058] A synthetic method for finasteride, comprising the steps of:

[0059] (1), the synthesis of 3-carbonyl-4-androstene-17β-carboxylic acid

[0060] Progesterone (3.2 g, 10.0 mmol) was dissolved in dioxane (20 mL). At low temperature, top up with Br 2 (1.52g, 9.5mmol) and 15% sodium hydroxide solution (4mL). After dropping, react for 6 hours. Pour into ice water (7 mL), extract the aqueous layer with ethyl acetate (10 mL×3), combine the organic phases, wash with appropriate amount of saturated sodium bicarbonate solution and saturated sodium chloride solution, and dry over anhydrous sodium sulfate. The solvent was evaporated to dryness under reduced pressure, and the residue was recrystallized from ethyl acetate to give white crystals of 3-carbonyl-4-androstene-17β-carboxylic acid (2.62g, yield 83%), mp 246~247°C (document mp 245~248℃);

[0061] (2), the synthesis of N-tert-butyl-3-carbonyl-4-androstene-17β-carboxamide

[0062] 3-carbonyl-4-androstene-17β-carboxylic a...

Embodiment 3

[0074] A synthetic method for finasteride, comprising the steps of:

[0075] (1), the synthesis of 3-carbonyl-4-androstene-17β-carboxylic acid

[0076] Progesterone (31.5 g, 100.0 mmol) was dissolved in dioxane (200 mL). At low temperature, top up with Br 2 (16.00 g, 100.0 mmol) and 15% sodium hydroxide solution (40 mL). After dropping, react for 6 hours. Pour into ice water (70 mL), extract the aqueous layer with ethyl acetate (40 mL×3), combine the organic phases, wash with appropriate amount of saturated sodium bicarbonate solution and saturated sodium chloride solution, and dry over anhydrous sodium sulfate. The solvent was evaporated to dryness under reduced pressure, and the residue was recrystallized from ethyl acetate to obtain white crystal 3-carbonyl-4-androstene-17β-carboxylic acid (28.10 g, yield 89%), mp 246~247 ° C (document mp 245~248℃);

[0077] (2), the synthesis of N-tert-butyl-3-carbonyl-4-androstene-17β-carboxamide

[0078] 3-carbonyl-4-androstene-17β...

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Abstract

The invention discloses a synthesis method of finasteride, which comprises the following steps that: taking inexpensive luteosterone and the like as the raw materials to finally prepare finasteride through 6 steps of synthetic reaction, i.e. the synthesis of 3- carbonyl-4- androstene-17beta-carboxylic acid, the synthesis of N-tertiary-butyl-3- carbonyl-4- androstene-17beta-formamide, the synthesis of N-tertiary-butyl-5- carbonyl-17beta- carbamoyl-A-lost carbon-3,5-cracking- androstane-3-acid, the synthesis of N-tertiary-butyl-3-carbonyl-4- aza-5- androstene-17beta-formamide, the synthesis of N-tertiary-butyl-3- carbonyl-4- aza-5alpha- androstane-17beta- formamide, and the synthesis of finasteride. The synthesis process has the advantages of inexpensive and easily available raw materials and stable yield, is applicable to industrial production, and the product quality meets the pharmacopeia standards.

Description

technical field [0001] The invention relates to a method for synthesizing a compound, in particular to a method for synthesizing finasteride. Background technique [0002] Finasteride is a selective but not specific type I and type II 5α-reductase inhibitor developed by Merck, USA. It is the first 5α-reductase inhibitor to be used clinically [1] . There are mainly 3 synthetic routes of finasteride [2-8] . They all use pregnenolone as the starting material to synthesize the important intermediate 3-carbonyl-4-androstene-17β-carboxylic acid. The main difference is that after the intermediate 3-carbonyl-4-androstene-17β-carboxylic acid is obtained, the sequence of ring opening, the reagents used for the synthesis of amides, the selection of hydrogenation reaction catalysts, and the 1,2-position dehydrogenation reaction. The choice of oxidizing agent. However, there are problems such as expensive raw materials, high synthesis cost, and low reaction yield (total yield is on...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J73/00
Inventor 姚志艺蒋晟孙小玲
Owner SHANGHAI INST OF TECH
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