Tetrahydrofuran → (3beta,5beta,15alpha,16alpha)-15,16-Dihydro-3,5-dihydroxy-3'H-cycloprop(15,16)androsta-6,15-dien-17-one

HRID 1649469

Reaction equation

HRID 1649469 reaction equation
Cl[C@@H:2]1[C@H:19]2[O:20][C@:18]32[C@:13]([CH3:22])([CH2:14][CH2:15][C@H:16]([OH:21])[CH2:17]3)[C@@H:12]2[C@@H:3]1[C@H:4]1[C@@:8]([CH2:10][CH2:11]2)([CH3:9])[C:7](=[O:23])[C@H:6]2[CH2:24][C@@H:5]12.O1CCCC1>C(O)(=O)C.[Zn]>[OH:21][C@H:16]1[CH2:15][CH2:14][C@@:13]2([CH3:22])[C@:18]([OH:20])([CH:19]=[CH:2][C@@H:3]3[C@@H:12]2[CH2:11][CH2:10][C@@:8]2([CH3:9])[C@H:4]3[C@@H:5]3[CH2:24][C@@H:6]3[C:7]2=[O:23])[CH2:17]1

Participants

5

Reactant 2

HCID 8028TetrahydrofuranHCID 130759667alpha-Chloro-5,6beta-epoxy-3beta-hydroxy-15beta,16beta-methylene-5beta-androstan-17-one

Product 1

HCID 13075974(3beta,5beta,15alpha,16alpha)-15,16-Dihydro-3,5-dihydroxy-3'H-cycloprop(15,16)androsta-6,15-dien-17-oneYield 94.4%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

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.

Workup

  1. filtrationThe zinc is then filtered off
  2. additionthe filtrate is diluted with methylene chloride
  3. washwashed with sodium bicarbonate solution and water
  4. dry with materialAfter drying over sodium sulfate
  5. concentrationthe product is concentrated under vacuum

Sources & evidence

ORD record
ord-a28a838e40c14be4b6889b559cd5de07
Source dataset
uspto-grants-1983_11
Patent number
US04416985

Linked notes

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