반응 #354822

ord-f55e237d9a924abca2eb4e12464cbcf6

반응 방정식

CC(C)=O.O=S(=O)(O)O.[O]=[Cr](=[O])=[O]
Jones reagent
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
→
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
title compound
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-androstane-3,11-dione

반응물

CC(C)=O.O=S(=O)(O)O.[O]=[Cr](=[O])=[O]
Jones reagent
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

시약

없음

용매

ClC(Cl)Cl
chloroform
CC(C)=O
acetone

반응 조건

상세 조건
See reaction.notes.procedure_details.

후처리

  1. 1
    세척washed with aqueous 10% sodium bicarbonate and water
  2. 2
    건조The chloroform solution was dried
  3. 3
    여과filtered
  4. 4
    기타evaporated
  5. 5
    기타to give a gum (238 mg.) which
  6. 6
    기타after purification by preparative thick layer chromatography

실험 절차

Jones reagent (0.4 ml.) was added to a solution of 3α-hydroxy-17β(3'-morpholinopropoxycarbonyl)-5α-androstan-11-one (325 mg.) in acetone (5 ml.). After stirring (20 min.) the reaction mixture was diluted with chloroform and washed with aqueous 10% sodium bicarbonate and water. The chloroform solution was dried, filtered and evaporated to give a gum (238 mg.) which, after purification by preparative thick layer chromatography, afforded the pure title compound; νmax.CHBr3 1703 (-C=O) and 1720 cm-1 (-COOR), (-OH absent).

출처

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