Sodium → HCID 12796465, compound

Participants

Reaction Steps

Sodium (2.7 g) was added portionwise to a stirred and refluxing solution of 2β-ethoxy-3α-hydroxy-17-methylene-5α-androstan-11-one 11-oxime (1.7 g) in propanol (100 ml) under nitrogen. The cooled reaction mixture was diluted with water and the precipitated solid (1.43 g) was collected by filtration. A portion of this material (300 mg) was purified by partitioning between 2 N-hydrochloric acid and ether when the insoluble hydrochloride which precipitated was collected by filtration and again partitioned between ether and 2 N-sodium hydroxide solution. The organic layer was washed, dried (Na2SO4) and evaporated to give the title compound as a froth (180 mg), [α]D +1.6°.

Provenance & Evidence