반응 #354806

ord-0d978c6325eb4f3c824f618eb42154a7

반응 방정식

C[C@]12CCC(=O)C[C@@H]1CC[C@H]1[C@@H]3CC[C@H](C(=O)OCCCN4CCOCC4)[C@@]3(C)CC(=O)[C@@H]12
17β(3'-morpholinopropoxycarbonyl)-5α-androstan-3,11-dione
CCN(CC)CC
triethylamine
→
C[C@]12CC[C@@H](O)C[C@@H]1CC[C@H]1[C@@H]3CC[C@H](C(=O)OCCCN4CCOCC4)[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)OCCCN4CCOCC4)[C@@]3(C)CC(=O)[C@@H]12
3α-Hydroxy-17β-(3'-morpholinopropoxycarbonyl)-5α-androstan-11-one

반응물

C[C@]12CCC(=O)C[C@@H]1CC[C@H]1[C@@H]3CC[C@H](C(=O)OCCCN4CCOCC4)[C@@]3(C)CC(=O)[C@@H]12
17β(3'-morpholinopropoxycarbonyl)-5α-androstan-3,11-dione
CCN(CC)CC
triethylamine

시약

Cl.Cl.O.[Cl][Ir]([Cl])([Cl])[Cl]
chloroiridic acid

용매

CC(C)O
isopropanol

반응 조건

상세 조건
See reaction.notes.procedure_details.

후처리

  1. 1
    workup.ADDITIONto the addition
  2. 2
    온도After refluxing for 7 hr
  3. 3
    기타, isolation of the product afforded a gum (150 mg.) which
  4. 4
    기타after purification by preparative t.l.c

실험 절차

A solution of 17β(3'-morpholinopropoxycarbonyl)-5α-androstan-3,11-dione (140 mg.) in isopropanol (1 ml.) was added to a "stock" solution of the chloroiridic acid reagent (7 ml.) which had been neutralised to ca. pH 6 with triethylamine immediately prior to the addition. After refluxing for 7 hr., isolation of the product afforded a gum (150 mg.) which, after purification by preparative t.l.c., gave the title compound as a white froth; 112 mg., [α]D + 51° (c, 0.6,).

출처

DOI: 10.6084/m9.figshare.5104873.v1특허: US03943124uspto-grants-1976_03