Potassium Acetate → 11-Deoxyprednisone acetate

HRID 1285292Notes

Reaction equation

HRID 1285292 reaction equation
Br[CH2:2][C:3](=[O:25])[C@:4]1([OH:24])[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])[CH:14]=[CH:15]2)[CH2:10][CH2:9]3)[CH2:6][CH2:5]1.[C:26]([O-:29])(=[O:28])[CH3:27].[K+]>CC(C)=O.C(OCC)(=O)C>[C:26]([O:29][CH2:2][C:3](=[O:25])[C@:4]1([OH:24])[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])[CH:14]=[CH:15]2)[CH2:10][CH2:9]3)[CH2:6][CH2:5]1)(=[O:28])[CH3:27]

Participants

5

Reactant 2

HCID 517044Potassium AcetateHCID 53908225HCID 53908225, compound

Product 1

HCID 22711011-Deoxyprednisone acetateYield 91.3%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 8857Ethyl AcetateSolvent

Procedure

3.0 g of 21-bromo-17-hydroxy-1,4-pregnadiene-3,20-dione is stirred in 60 ml of acetone with 3.0 g of potassium acetate at 50° C. The reaction mixture is introduced into ice water after 2 hours, the thus-precipitated product is suctioned off, dissolved in ethyl acetate, washed with water, and dried over sodium sulfate, thus producing 2.6 g of 21-acetoxy-17-hydroxy-1,4-pregnadiene-3,20-dione, mp 214° C.

Workup

  1. washwashed with water
  2. dry with materialdried over sodium sulfate

Sources & evidence

ORD record
ord-74157c283fcf47a295243aaa9cd3ea7f
Source dataset
uspto-grants-1986_01
Patent number
US04567002

Reaction notes

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