Ethyl bromoacetate → 17beta-Ethoxycarbonylmethoxycarbonyl-3alpha-hydroxy-5alpha-androstan-11-one

Participants

Reaction Steps

Triethylamine (4.5 mmole) was added to a solution of 3α-hydroxy-5α-androstan-11-one 17β-carboxylic acid (1.025g.,) in warm acetone (50 ml.) followed by ethyl bromoacetate (6 mmole) and the reaction mixture stood at room temperature overnight. The reaction was completed by refluxing for 1 hr., evaporating to dryness and partitioning the residue between water and ether. The ethereal solution was washed with water, dried, and evaporated to give a residue (1.61g.) which was purified by preparative t.l.c. to afford the pure title compound; [α]D + 76°.

Provenance & Evidence