HCID 70583577, compound → HCID 70583955, compound

Participants

Reaction Steps

A 1.5 M solution of methyl lithium in ether (20 ml) was added to a cooled solution of 11α-N,N-dimethylamino-2β-ethoxy-3α-hydroxy-5α-androstan-17-one 17-p-toluenesulphonylhydrazone (1.2 g) in dry tetrahydrofuran (100 ml). The mixture was kept at room temperature for three days and then most of the solvent was evaporated in vacuo. The residue was acidified with 2 N-hydrochloric acid, washed with ether, and the aqueous layer was then basified with 2 N-sodium hydroxide and extracted into ether. The washed and dried (Na2SO4) extract was evaporated in vacuo and the residue was purified by chromatography over silica (ethyl acetate-petroleum ether 1:1) and crystallization from aqueous methanol to give the title compound m.p. 51°-54°, [α]D -23.8°.

Provenance & Evidence