Synthesis and Crystal Structure of 3β-Acetoxy-5α-bromo-6β-hydroxyandrostan-17-one

Abstract

The title steroid 3β-acetoxy-5α-bromo-6β-hydroxyandrostan-17-one 1 was synthesized from the reaction of 3β-acetoxy-5-androstene-17-one with N-bromosuccinimide (NBS) and characterized by FT-IR, 1H-NMR, EI-MS and ESI-HRMS techniques. The structure of the compound was also determined crystallographically. The crystal structure was solved by direct methods and refined by full-matrix least-squares. It crystallized with two molecules in the asymmetric unit in the triclinic space group P1 with a = 7.0518(9), b = 10.1362(16), c = 15.3472(19) A, α = 100.579(8), β = 99.354(6), γ = 109.267(5)°, V = 988.1(2) A3, D x = 1.436 g cm−3, respectively (R 1 = 0.0262 and wR 2 = 0.0468 for 5273 reflections [I > 2σ(I)]). Three-six-membered rings A, B and C exist in chair conformation while the five-membered ring D displays an envelope conformation. The intermolecular interactions O–H···O link the molecules into a three dimensional network. The crystal structure was compared with our previously reported similar structures. The crystal structure of 3β-acetoxy-5α-bromo-6β-hydroxyandrostan-17-one prepared by halohydroxylation of 3β-acetoxy-5-androstene-17-one is presented in this work