Reacción #354795

ord-bb55f724df6f4344aa9065853756c0c4

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
CO
methanol
O=S(=O)(O)O
sulphuric acid
→
COC(=O)[C@H]1CC[C@H]2[C@@H]3CC[C@H]4C[C@H](O)[C@@H](OC)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](OC)C[C@]4(C)[C@H]3C(=O)C[C@]12C
3α-Hydroxy-2β-methoxy-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
CO
methanol
O=S(=O)(O)O
sulphuric acid

Reactivos

Ninguno

Disolventes

O
water

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    workup.ADDITIONAfter 30 minutes the solution was poured
  2. 2
    OtroThe precipitated product was isolated
  3. 3
    Lavadowashed with water
  4. 4
    Secadodried over sodium hydroxide in vacuo

Procedimiento

2α,3α-Epoxy-17β-methoxycarbonyl-5α-androstan-11-one (500 mg.) in warm dry methanol (30 ml.) was treated with concentrated sulphuric acid (0.15 ml.). After 30 minutes the solution was poured into stirred water. The precipitated product was isolated, washed with water and dried over sodium hydroxide in vacuo to give fairly pure title compound (420 mg.) as a white powder; m.p. 170°-182°; [α]D + 68°,

Fuente

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