반응 #354800

ord-24d9ffb035cb42a5b24446cbd0a21627

반응 방정식

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-11-oxo-5α-androstane-17β-carboxylic acid
CCCC[N+](CCCC)(CCCC)CCCC.[OH-]
tetra-butyl ammonium hydroxide
O=C([O-])O.[K+]
potassium bicarbonate
CC(=O)OCCl
chloromethyl acetate
[I-].[Na+]
sodium iodide
→
CC(=O)OCOC(=O)[C@H]1CC[C@H]2[C@@H]3CC[C@H]4C[C@H](O)CC[C@]4(C)[C@H]3C(=O)C[C@]12C
title compound
CC(=O)OCOC(=O)[C@H]1CC[C@H]2[C@@H]3CC[C@H]4C[C@H](O)CC[C@]4(C)[C@H]3C(=O)C[C@]12C
17β-Acetoxymethoxycarbonyl-3α-hydroxy-5α-androstan-11-one

반응물

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-11-oxo-5α-androstane-17β-carboxylic acid
CCCC[N+](CCCC)(CCCC)CCCC.[OH-]
tetra-butyl ammonium hydroxide
O=C([O-])O.[K+]
potassium bicarbonate
CC(=O)OCCl
chloromethyl acetate
[I-].[Na+]
sodium iodide

시약

없음

용매

CC(C)=O
acetone

반응 조건

상세 조건
See reaction.notes.procedure_details.

후처리

  1. 1
    기타The mixture was evaporated to small volume
  2. 2
    workup.ADDITIONdiluted with ethyl acetate
  3. 3
    세척washed with water
  4. 4
    건조dried (Na2SO4)
  5. 5
    기타evaporated to a residue
  6. 6
    기타Purification by preparative t.l.c

실험 절차

3α-Hydroxy-11-oxo-5α-androstane-17β-carboxylic acid (1g.) was warmed with tetra-butyl ammonium hydroxide (1.94g. Of 40% solution) and acetone (10 ml.) to effect solution. The solution was refluxed with sodium iodide (100 mg.). potassium bicarbonate (150 mg.) and chloromethyl acetate (0.6 ml.) for 2 hours. The mixture was evaporated to small volume, diluted with ethyl acetate, washed with water, dried (Na2SO4) and evaporated to a residue. Purification by preparative t.l.c. gave title compound (less polar band) (318 mg.) as white foam; [α]D + 52°.

출처

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