Réaction #93693

ord-7ff38eea68f44483bc43bbb2373e964e

Équation de réaction

CC(C)(C)[Si](C)(C)O[C@H]1CC[C@]2(C)[C@H]3CC[C@]4(C)C(=O)[C@H]5C[C@H]5[C@H]4[C@@H]3[C@H](Cl)[C@H]3O[C@]32C1
3β-(tert.-butyldimethylsilyloxy)-7α-chloro-5,6β-epoxy-15β,16β-methylene-5β-androstan-17-one
CO
methanol
O=S(=O)(O)O
sulfuric acid
→
CC(C)OC(C)C
diisopropyl ether
C[C@]12CC[C@H]3[C@@H]([C@H](Cl)[C@H]4O[C@]45C[C@@H](O)CC[C@]35C)[C@@H]1[C@@H]1C[C@@H]1C2=O
7α-chloro-5,6β-epoxy-3β-hydroxy-15β,16β- methylene-5β-androstan-17-one

Réactifs

CC(C)(C)[Si](C)(C)O[C@H]1CC[C@]2(C)[C@H]3CC[C@]4(C)C(=O)[C@H]5C[C@H]5[C@H]4[C@@H]3[C@H](Cl)[C@H]3O[C@]32C1
3β-(tert.-butyldimethylsilyloxy)-7α-chloro-5,6β-epoxy-15β,16β-methylene-5β-androstan-17-one
CO
methanol
O=S(=O)(O)O
sulfuric acid

Réactifs

Aucun

Solvants

CCOCC
ether
C1CCOC1
tetrahydrofuran

Conditions de réaction

Conditions détaillées
See reaction.notes.procedure_details.

Traitement

  1. 1
    Lavagewashed with saturated sodium bicarbonate solution and water
  2. 2
    Séchagedried over sodium sulfate
  3. 3
    Concentrationconcentrated under vacuum

Mode opératoire

142 g of 3β-(tert.-butyldimethylsilyloxy)-7α-chloro-5,6β-epoxy-15β,16β-methylene-5β-androstan-17-one is dissolved in 400 ml of tetrahydrofuran and 400 ml of methanol and stirred with 1,000 ml of 8% strength sulfuric acid for 1.5 hours at room temperature. The mixture is then diluted with ether, washed with saturated sodium bicarbonate solution and water, dried over sodium sulfate, and concentrated under vacuum. By trituration of the resultant solid with diisopropyl ether, 108 g of 7α-chloro-5,6β-epoxy-3β-hydroxy-15β,16β- methylene-5β-androstan-17-one is obtained, mp 173° C.

Source

DOI: 10.6084/m9.figshare.5104873.v1Brevet: US04614616uspto-grants-1986_09