Sodium Hydroxide → HCID 22804191, compound

Participants

Reaction Steps

25 g (0.056 mole) of 2β-chloro-3α-hydroxy-17-oxo-16β-piperidino-5α-androstane-hydrochloride (Example 14) are dissolved in the mixture of 52 ml of methylene chloride and 125 ml of methanol. Under vigorous stirring 2.75 g (0.069 mole) of pulverized sodium hydroxide are added at a temperature of 15°-20° C. 12.5 g (0.33 mole) of sodium borohydride are also added to the solution. The product precipitated immediately. The crystalline solution is stirred for 5 hours, whereafter the product is filtered and washed with water. The mother liquor is evaporated at reduced pressure at a temperature of below 30° C, the residue is triturated with water, the mixture is filtered and the second crop above the filter is washed with water. The two fractions are combined, dried in vacuo at 50° C, followed by recrystallization from acetone. Yield: 20.2 g (88%) of 2β-chloro-3α,17β-dihydroxy-16β-piperidine-5α-androstane; m.p. 232°-234° C.

Provenance & Evidence