Sodium Hydroxide → 3alpha-Hydroxy-16alpha-methyl-5alpha-androstan-11-one 17beta-carboxylic acid

참여 물질

반응 단계

A solution of sodium hydroxide (7.35g.) in water, (55 ml.) was stirred at -5° and bromine added slowly maintaining the temperature between -5° and 0°. Cold dioxan (45 ml.) was added and the pale yellow sodium hypobromite solution stirred at 0° until required. 3α-Hydroxy-16α-methyl-5α-pregnane-11, 20-dione (5.0g.) was dissolved in dioxan (200 ml.) and water (55 ml.). The hypobromite solution was added over 5 min. and the resulting mixture kept between 5° and 10° with stirring for 3 hr. Sodium sulphite heptahydrate (2.8g.) in water (15 ml.) was added and the solution refluxed for 15 min. The mixture was acidified and concentrated to incipient crystallisation before pouring into water (1 1.). Filtration afforded the title compound (3.85g.); m.p. 265°-268°.

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