Simultaneously Rapid Deprotection of 3-acyloxy groups and reduction of D-ring ketones (nitrile) of steroids using DIBAL-H/NiCl₂

Abstract

An efficient preparation of hydroxysteroids by a one-pot, simultaneously rapid deprotection of 3-acyloxy groups and reduction of D-ring ketones (nitrile) of steroids using DIBAL-H in the presence of NiCl 2 (10 mol %) is described. The attractive features of this procedure for the preparation of the hydroxysteroid derivatives are the mild reaction conditions, short reaction time, excellent yields, clean reaction profiles, and an inexpensive catalyst system. Scheme 1 Simultaneously deprotection of 3-acyloxy groups and reduction of 17-ketone of 1a under varies selected reaction conditions.

Molecular docking simulation studies on potent butyrylcholinesterase inhibitors obtained from microbial transformation of dihydrotestosterone

“…: 153–155°C (154–157°C [ 30 ]). [α] 25 D : -72.0, c = 0.034, MeOH (+6.20, c = 0.55, CHCl 3 [ 31 ]). 1 H-NMR (CD 3 OD, 400 MHz): δ 0.97, m, 1.72 a , m (H-1); 1.38, m, 1.73 a , m (H-2); 3.49, m (H-3); 1.26, m, 1.50, m (H-4); 1.10, m (H-5); 1.28 a , m, 1.31 a , m (H-6); 0.89, m, 1.68, m (H-7); 1.40, m (H-8); 0.64, ddd ( J 9a,8a = 14.8 Hz, J 9a,11a = 10.8 Hz, J 9a,11e = 4.4 Hz) (H-9); 1.30 a , m, 1.56 a , m (H-11); 1.02, m, 1.79, m (H-12); 0.92, m (H-14); 1.24, m, 1.57 a , m (H-15); 1.45, m, 1.95, m (H-16); 3.54, t ( J 17a,16a/16e = 8.4 Hz) (H-17); 0.71, s (H-18); 0.83, s (H-19), (a = exchangeable assignments).…”