20beta-Hydroxyprogesterone → HCID 57182055, compound

HRID 1659836Notes

Reaction equation

HRID 1659836 reaction equation
[OH:1][C@@H:2]([C@@H:4]1[C@:21]2([CH3:22])[C@H:7]([C@H:8]3[C@H:18]([CH2:19][CH2:20]2)[C@:16]2([CH3:17])[C:11](=[CH:12][C:13](=[O:23])[CH2:14][CH2:15]2)[CH2:10][CH2:9]3)[CH2:6][CH2:5]1)[CH3:3].CC(C)([O-])C.[K+]>CS(C)=O>[OH:1][C@@H:2]([C@@H:4]1[C@:21]2([CH3:22])[C@H:7]([C@H:8]3[C@H:18]([CH2:19][CH2:20]2)[C@:16]2([CH3:17])[C:11]([CH2:12][C:13](=[O:23])[CH2:14][CH2:15]2)=[CH:10][CH2:9]3)[CH2:6][CH2:5]1)[CH3:3]

Participants

4

Reactant 2

HCID 9274720beta-HydroxyprogesteroneHCID 23665647Potassium tert-butoxide

Product 1

HCID 57182055HCID 57182055, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A solution of 34.8 g (0.11 mol) of (20R)-20-hydroxy-pregn-4-en-3-one in 300 ml of dimethyl sulphoxide is treated with 18.7 g (0.16 mol) of potassium tert. butoxide and stirred for 4 hours at room temperature under argon. The red-brown mixture is poured on to 1 kg of ice and the product is extracted with methylene chloride. The extract is washed with water, dried over sodium sulphate and evaporated in a water-jet vacuum. The residue is chromatographed on 1 kg of silica gel with hexane/ether/methylene chloride (7:2:1) and gives 7.3 g (21%) of uniform, crystalline (20R)-20-hydroxy-pregn-5-en-3-one. The analytical sample is obtained by recrystallisation from ethanol/methylene chloride; melting point 171°-175° C.; [α]D25 =-33.2° (c=0.5 in chloroform).

Workup

  1. extractionthe product is extracted with methylene chloride
  2. washThe extract is washed with water
  3. dry with materialdried over sodium sulphate
  4. customevaporated in a water-jet vacuum
  5. customThe residue is chromatographed on 1 kg of silica gel with hexane/ether/methylene chloride (7:2:1)

Sources & evidence

ORD record
ord-c2f6f80565ad4ee8b69d0612a94303c1
Source dataset
uspto-grants-1981_12
Patent number
US04305881

Reaction notes

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