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

HRID 2418135Notes

Reaction equation

HRID 2418135 reaction equation
C([O:4][C@H:5]1[CH2:22][CH2:21][C@@:20]2([CH3:23])[C@:7]([OH:26])([CH:8]=[CH:9][C@@H:10]3[C@@H:19]2[CH2:18][CH2:17][C@@:15]2([CH3:16])[C@H:11]3[C@@H:12]3[CH2:25][C@@H:13]3[C:14]2=[O:24])[CH2:6]1)(=O)C.C(=O)([O-])[O-].[K+].[K+]>CO.C(OCC)C>[OH:4][C@H:5]1[CH2:22][CH2:21][C@@:20]2([CH3:23])[C@:7]([OH:26])([CH:8]=[CH:9][C@@H:10]3[C@@H:19]2[CH2:18][CH2:17][C@@:15]2([CH3:16])[C@H:11]3[C@@H:12]3[CH2:25][C@@H:13]3[C:14]2=[O:24])[CH2:6]1

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 70505457HCID 70505457, compound

Product 1

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

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Procedure

A solution of 3β-acetoxy-5-hydroxy-15β,16β-methylene-5β-androst-6-en-17-one in 300 ml of methanol is stirred with 15 g of potassium carbonate for 30 minutes at room temperature. The reaction solution is diluted with diethyl ether, washed with water, dried, and evaporated, thus obtaining 27 g of 3β,5-dihydroxy-15β,16β-methylene-5β-androst-6-en-17-one, mp 187°-190° C., (acetone).

Workup

  1. washwashed with water
  2. customdried
  3. customevaporated

Sources & evidence

ORD record
ord-5a4f1c622ea847a395c032620fccb4fd
Source dataset
uspto-grants-1984_09
Patent number
US04472310

Reaction notes

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