Reacción #93694

ord-4f6f033bf183440a905cf0a17ebf7a0c

Ecuación de reacción

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
C1CCOC1
tetrahydrofuran
→
C[C@]12CC[C@H]3[C@@H](C=C[C@]4(O)C[C@@H](O)CC[C@]34C)[C@@H]1[C@@H]1C[C@@H]1C2=O
3β,5-dihydroxy-15β,16β-methylene-5β-androst-6-en-17-one
Rendimiento 94.4%

Reactantes

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
C1CCOC1
tetrahydrofuran

Reactivos

[Zn]
zinc

Disolventes

CC(=O)O
acetic acid

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    FiltraciónThe zinc is then filtered off
  2. 2
    workup.ADDITIONthe filtrate is diluted with methylene chloride
  3. 3
    Lavadowashed with sodium bicarbonate solution and water
  4. 4
    SecadoAfter drying over sodium sulfate
  5. 5
    Concentraciónthe product is concentrated under vacuum

Procedimiento

107.5 g of 7α-chloro-5,6β-epoxy-3β-hydroxy-15β,16β-methylene-5β-androstan-17-one is dissolved in 500 ml of acetic acid and 500 ml of tetrahydrofuran and, after the addition of 324 g of zinc dust in three portions, stirred at room temperature for 16 hours. The zinc is then filtered off, the filtrate is diluted with methylene chloride, and washed with sodium bicarbonate solution and water. After drying over sodium sulfate, the product is concentrated under vacuum. By trituration of the thus-obtained solid with ethyl acetate, 91.5 g of 3β,5-dihydroxy-15β,16β-methylene-5β-androst-6-en-17-one is produced, mp 196° C.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US04614616uspto-grants-1986_09