Reacción #354815

ord-eab4cb42023140f1ac5d110dee3d3b59

Ecuación de reacción

C[C@]12CC=CC[C@@H]1CC[C@H]1[C@@H]3CC[C@H](C(=O)O)[C@@]3(C)CC(=O)[C@@H]12
5α-androst-2-en-11one 17β-carboxylic acid
O=C(OO)c1cccc(Cl)c1
m-chloroperbenzoic acid
→
C[C@]12C[C@H]3O[C@H]3C[C@@H]1CC[C@H]1[C@@H]3CC[C@H](C(=O)O)[C@@]3(C)CC(=O)[C@@H]12
title compound
C[C@]12C[C@H]3O[C@H]3C[C@@H]1CC[C@H]1[C@@H]3CC[C@H](C(=O)O)[C@@]3(C)CC(=O)[C@@H]12
2α,3α-epoxy-5α-androstan-11-one-17β-carboxylic acid

Reactantes

C[C@]12CC=CC[C@@H]1CC[C@H]1[C@@H]3CC[C@H](C(=O)O)[C@@]3(C)CC(=O)[C@@H]12
5α-androst-2-en-11one 17β-carboxylic acid
O=C(OO)c1cccc(Cl)c1
m-chloroperbenzoic acid

Reactivos

Ninguno

Disolventes

ClC(Cl)Cl
chloroform
ClC(Cl)Cl
chloroform

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    Lavadoto washing with 10% aqueous sodium bicarbonate and water
  2. 2
    SecadoThe chloroform solution was dried
  3. 3
    Filtraciónfiltered
  4. 4
    Otroevaporated
  5. 5
    Otroto give a foam (1.04g.) which

Procedimiento

A solution of 5α-androst-2-en-11one 17β-carboxylic acid (1.397 g.) and m-chloroperbenzoic acid (850 mg.) in chloroform (20 ml.) was stirred at room temperature for 3.25 hr. and then diluted with chloroform (75 ml.) prior to washing with 10% aqueous sodium bicarbonate and water. The chloroform solution was dried, filtered and evaporated to give a foam (1.04g.) which, after preparative t.l.c. afforded the pure title compound as a foam; [α]D + 69°, (c 0.3).

Fuente

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