Potassium Bicarbonate → Deoxycorticosterone

HRID 1032027Notes

Reaction equation

HRID 1032027 reaction equation
ClC[C:3](=[O:27])[C@:4]1(OC=O)[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.[C:28](=O)(O)[O-:29].[K+]>CO.O>[OH:29][CH2:28][C:3](=[O:27])[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

Participants

5

Reactant 2

HCID 516893Potassium BicarbonateHCID 1360479021-Chloro-17-formyloxy-4-pregnene-3,20-dione

Product 1

HCID 6166Deoxycorticosterone

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

At room temperature, 1.6 g of 21-chloro-17- formyloxy-4-pregnene-3,20-dione is stirred in a mixture of 60 ml of methanol and 9 ml of water with 500 mg of potassium bicarbonate After one hour, the reaction mixture is stirred into ice water. The thus-precipitated product is suctioned off, washed with water, and dried over sodium sulfate, yielding 1.3 g of 21-chloro-17™hydroxy-4-pregnene-3,20-dione; mp 239.4° C.

Workup

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

Sources & evidence

ORD record
ord-25387410bc2e4383a70c2514740b037a
Source dataset
uspto-grants-1990_09
Patent number
US04956482

Reaction notes

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