Reacción #310613

ord-7a9d29520beb4a72857da4445430b7b6

Ecuación de reacción

Cc1ccc(S(=O)(=O)O)cc1
Toluene-4-sulphonic acid
COC(=O)[C@H]1CC[C@H]2[C@@H]3CC[C@H]4CC=CC[C@]4(C)[C@H]3[C@H](N)C[C@]12C
methyl 11α-amino-5α-androst-2-ene-17β-carboxylate
O=C(OO)c1cccc(Cl)c1
m-chloroperoxybenzoic acid
→
N
NH3
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]3[C@H](N)C[C@]12C
title compound
Rendimiento 70.4%
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]3[C@H](N)C[C@]12C
Methyl 11α-amino-2α,3α-epoxy-5α-androstane-17β-carboxylate
Rendimiento 70.4%

Reactantes

Cc1ccc(S(=O)(=O)O)cc1
Toluene-4-sulphonic acid
COC(=O)[C@H]1CC[C@H]2[C@@H]3CC[C@H]4CC=CC[C@]4(C)[C@H]3[C@H](N)C[C@]12C
methyl 11α-amino-5α-androst-2-ene-17β-carboxylate
O=C(OO)c1cccc(Cl)c1
m-chloroperoxybenzoic acid

Reactivos

Ninguno

Disolventes

ClCCCl
1,2-dichloroethane

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    LavadoThe mixture was washed with NaHSO3 solution, 5% NaHCO3 solution and water
  2. 2
    ExtracciónThe aqueous phases were extracted with dichloromethane
  3. 3
    Otrothe combined organic phase was dried
  4. 4
    Otroevaporated
  5. 5
    Otroto leave a foam which
  6. 6
    Otrowas purified by preparative t.l.c

Procedimiento

Toluene-4-sulphonic acid (570 mg) was added to a solution of methyl 11α-amino-5α-androst-2-ene-17β-carboxylate (1.0 g) in 1,2-dichloroethane (25 ml). After 0.5 h m-chloroperoxybenzoic acid (810 mg) was added and the mixture was left for a further 2 h. The mixture was washed with NaHSO3 solution, 5% NaHCO3 solution and water. The aqueous phases were extracted with dichloromethane and the combined organic phase was dried and evaporated to leave a foam which was purified by preparative t.l.c. in MeOH: 0.88 NH3 (50:1) to give the title compound (369 mg) as a foam [α]D +44°, νmax 1722 cm-1.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US04353898uspto-grants-1982_10