Water → HCID 86584404, compound

Participants

Reaction Steps

Prepare O93 from O92 by treating with acetic anhydride as described for the synthesis of J62 in example 10a, and then treat O93 with sodium borohydride to provide O94 as described for the preparation of J63 in example 10b. Add t-butyldimethylsilyl chloride (16.44 g, 109.1 mmol), 4-dimethylaminopyridine (0.62 g, 5.20 mmol) and triethylamine (15.9 mL, 114.3 mmol) to a stirred solution of estr-5-ene-3β,17β-diol 17-acetate (O94, 33.1 g, 103.9 mmol, Campbell, J. A. and Babcock, J. C., 1971, U.S. Pat. No. 3,597,418) in anhydrous DMF (350 mL) under nitrogen. Stir the resultant suspension at room temperature for 3 days and then pour into vigorously stirred water (2.5 L). Filter the resultant suspension to give 3β-[[(1,1-dimethylethyl)dimethylsilyl]oxy]estr-5-en-17β-ol 17 acetate (O95) as an off-white solid.

Provenance & Evidence