Reacción #70354

ord-7127e0140cd24d569a64493ba359a420

Ecuación de reacción

C[C@]12CC[C@@H](SC3CCNC3)CC1C(=O)C[C@@H]1[C@@H]2CC[C@]2(C)C(=O)CC[C@@H]12.O=C(O)/C=C/C(=O)O
3α-[3-(RS)-pyrrolidinylthio]androstane-6,17-dione fumarate
Cl.NO
hydroxylamine hydrochloride
→
C[C@]12CC[C@@H](SC3CCNC3)CC1/C(=N/O)C[C@@H]1[C@@H]2CC[C@]2(C)C(=O)CC[C@@H]12.O=C(O)/C=C/C(=O)O
title compound
C[C@]12CC[C@@H](SC3CCNC3)CC1/C(=N/O)C[C@@H]1[C@@H]2CC[C@]2(C)C(=O)CC[C@@H]12.O=C(O)/C=C/C(=O)O
3α-[3-(RS)-Pyrrolidinylthio]-6-(E)-hydroxyiminoandrostane-17-one fumarate

Reactantes

C[C@]12CC[C@@H](SC3CCNC3)CC1C(=O)C[C@@H]1[C@@H]2CC[C@]2(C)C(=O)CC[C@@H]12.O=C(O)/C=C/C(=O)O
3α-[3-(RS)-pyrrolidinylthio]androstane-6,17-dione fumarate
Cl.NO
hydroxylamine hydrochloride

Reactivos

Ninguno

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    OtroThe title compound was prepared
  2. 2
    OtroThe crude product was purified by flash chromatography (SiO2, CH2Cl2/MeOH/NH3 9/1/0.1)
  3. 3
    workup.ADDITIONTo the concentrated fractions the stoichiometric amount of fumaric acid in MeOH was added
  4. 4
    workup.ADDITIONAfter addition of EtOAc
  5. 5
    Filtraciónthe precipitate was filtered

Procedimiento

The title compound was prepared following the procedure described in Example 1 and starting from 3α-[3-(RS)-pyrrolidinylthio]androstane-6,17-dione fumarate (I-dc, Example 81, 115 mg) and hydroxylamine hydrochloride (20 mg). The crude product was purified by flash chromatography (SiO2, CH2Cl2/MeOH/NH3 9/1/0.1). To the concentrated fractions the stoichiometric amount of fumaric acid in MeOH was added. After addition of EtOAc, the precipitate was filtered to give the title compound I-dd as a white solid in 65% yield. 1H-NMR (300 MHz, DMSO-d6, ppm from TMS): δ 10.72 (1H, bs), 6.42 (1H, m), 4.69 (1H, m), 3.57 (1H, m), 3.30-3.10 (6H, m), 2.40-0.95 (20H, m), 0.76 (3H, s), 0.63 (3H, s).

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US08536160B2uspto-grants-2013_09