3alpha-Hydroxy-17beta(3'-morpholinopropoxycarbonyl)-5alpha-androstan-11-one → 17beta(3'-Morpholinopropoxycarbonyl)-5alpha-androstan-3,11-dione

HRID 267640Notes

Reaction equation

HRID 267640 reaction equation
CC(C)=O.OS(O)(=O)=O.O=[Cr](=O)=O.[OH:14][C@@H:15]1[CH2:32][CH2:31][C@@:30]2([CH3:33])[C@@H:17]([CH2:18][CH2:19][C@@H:20]3[C@@H:29]2[C:28](=[O:34])[CH2:27][C@@:25]2([CH3:26])[C@H:21]3[CH2:22][CH2:23][C@@H:24]2[C:35]([O:37][CH2:38][CH2:39][CH2:40][N:41]2[CH2:46][CH2:45][O:44][CH2:43][CH2:42]2)=[O:36])[CH2:16]1>CC(C)=O.C(Cl)(Cl)Cl>[O:44]1[CH2:43][CH2:42][N:41]([CH2:40][CH2:39][CH2:38][O:37][C:35]([C@H:24]2[CH2:23][CH2:22][C@H:21]3[C@H:20]4[C@H:29]([C:28](=[O:34])[CH2:27][C@:25]23[CH3:26])[C@:30]2([CH3:33])[C@H:17]([CH2:16][C:15](=[O:14])[CH2:32][CH2:31]2)[CH2:18][CH2:19]4)=[O:36])[CH2:46][CH2:45]1

Participants

5

Reactant 2

HCID 227882623alpha-Hydroxy-17beta(3'-morpholinopropoxycarbonyl)-5alpha-androstan-11-oneHCID 131709961Jones' reagent

Product 1

HCID 2278824917beta(3'-Morpholinopropoxycarbonyl)-5alpha-androstan-3,11-dione

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6212ChloroformSolvent

Procedure

Jones reagent (0.4 ml.) was added to a solution of 3α-hydroxy-17β(3'-morpholinopropoxycarbonyl)-5α-androstan-11-one (325 mg.) in acetone (5 ml.). After stirring (20 min.) the reaction mixture was diluted with chloroform and washed with aqueous 10% sodium bicarbonate and water. The chloroform solution was dried, filtered and evaporated to give a gum (238 mg.) which, after purification by preparative thick layer chromatography, afforded the pure title compound; νmax.CHBr3 1703 (-C=O) and 1720 cm-1 (-COOR), (-OH absent).

Workup

  1. washwashed with aqueous 10% sodium bicarbonate and water
  2. dry with materialThe chloroform solution was dried
  3. filtrationfiltered
  4. customevaporated
  5. customto give a gum (238 mg.) which
  6. customafter purification by preparative thick layer chromatography

Sources & evidence

ORD record
ord-f55e237d9a924abca2eb4e12464cbcf6
Source dataset
uspto-grants-1976_03
Patent number
US03943124

Reaction notes

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