Reacción #354796

ord-f09a31a092c844289e62aadfc342ef16

Ecuación de reacción

COC(=O)[C@H]1CC[C@H]2[C@@H]3CC[C@H]4C[C@@H]5O[C@@H]5C[C@]4(C)[C@H]3C(=O)C[C@]12C
2α,3α-Epoxy-17β-methoxycarbonyl-5α-androstan-11-one
Br
hydrogen bromide
→
COC(=O)[C@H]1CC[C@H]2[C@@H]3CC[C@H]4C[C@H](O)[C@@H](Br)C[C@]4(C)[C@H]3C(=O)C[C@]12C
title compound
COC(=O)[C@H]1CC[C@H]2[C@@H]3CC[C@H]4C[C@H](O)[C@@H](Br)C[C@]4(C)[C@H]3C(=O)C[C@]12C
2β-Bromo-3α-hydroxy-17β-methoxycarbonyl-5α-androstan-11-one

Reactantes

COC(=O)[C@H]1CC[C@H]2[C@@H]3CC[C@H]4C[C@@H]5O[C@@H]5C[C@]4(C)[C@H]3C(=O)C[C@]12C
2α,3α-Epoxy-17β-methoxycarbonyl-5α-androstan-11-one
Br
hydrogen bromide

Reactivos

Ninguno

Disolventes

ClC(Cl)Cl
chloroform

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    LavadoAfter an hour the mixture was washed with an excess of aqueous sodium bicarbonate
  2. 2
    Secadowith water, was dried (MgSO4)
  3. 3
    Otroevaporated to a froth (628 mg.) Crystallisation from ethyl acetate/light petroleum

Procedimiento

2α,3α-Epoxy-17β-methoxycarbonyl-5α-androstan-11-one (500 mg.) in chloroform (32 ml.) was stirred with 48% aqueous hydrogen bromide (10 ml.). After an hour the mixture was washed with an excess of aqueous sodium bicarbonate and with water, was dried (MgSO4) and evaporated to a froth (628 mg.) Crystallisation from ethyl acetate/light petroleum afforded title compound (330 mg.) as colourless needles; m.p. 205°-208°; [α]D + 76°,

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US03943124uspto-grants-1976_03