Reacción #354802

ord-6f6388ad62094fc4995c14036fe5f63c

Ecuación de reacción

N#CCCl
chloroacetonitrile
CCN(CC)CC
Triethylamine
C[C@]12CC[C@@H](O)C[C@@H]1CC[C@H]1[C@@H]3CC[C@H](C(=O)O)[C@@]3(C)CC(=O)[C@@H]12
3α-hydroxy-5α-androstan-11-one 17β-carboxylic acid
N#CCCl
chloroacetonitrile
→
C[C@]12CC[C@@H](O)C[C@@H]1CC[C@H]1[C@@H]3CC[C@H](C(=O)OCC#N)[C@@]3(C)CC(=O)[C@@H]12
title compound
C[C@]12CC[C@@H](O)C[C@@H]1CC[C@H]1[C@@H]3CC[C@H](C(=O)OCC#N)[C@@]3(C)CC(=O)[C@@H]12
17β-Cyanomethoxycarbonyl-3α-hydroxy-5α-androstan-11-one

Reactantes

N#CCCl
chloroacetonitrile
CCN(CC)CC
Triethylamine
C[C@]12CC[C@@H](O)C[C@@H]1CC[C@H]1[C@@H]3CC[C@H](C(=O)O)[C@@]3(C)CC(=O)[C@@H]12
3α-hydroxy-5α-androstan-11-one 17β-carboxylic acid
N#CCCl
chloroacetonitrile

Reactivos

Ninguno

Disolventes

CC(C)=O
acetone

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    TemperaturaAfter refluxing this mixture for 3 hr
  2. 2
    Temperaturarefluxing
  3. 3
    OtroRemoval of the solvent
  4. 4
    Otroafforded a residue which
  5. 5
    Otrowas partitioned between ether and water
  6. 6
    LavadoThe ethereal solution was washed with water
  7. 7
    Secadodried (MgSO4)
  8. 8
    Otroevaporated
  9. 9
    Otroto give a foam (1.187g.) which
  10. 10
    Otrowas purified by preparative t.l.c

Procedimiento

Triethylamine (4.5 mmole) was added to a solution of 3α-hydroxy-5α-androstan-11-one 17β-carboxylic acid (1.025g.) in warm acetone (50 ml.) followed by chloroacetonitrile (6 mmole). After refluxing this mixture for 3 hr. further chloroacetonitrile (6 mmole) was added and refluxing continued for 4 hr. Removal of the solvent afforded a residue which was partitioned between ether and water. The ethereal solution was washed with water, dried (MgSO4) and evaporated, to give a foam (1.187g.) which was purified by preparative t.l.c. to afford the pure title compound; m.p. 142°-146°; [α]D + 74°,.

Fuente

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