Sodium Bicarbonate → 11beta-Chloroacetoxy-3alpha-hydroxy-5alpha-pregnan-20-one

HRID 1701458Notes

Reaction equation

HRID 1701458 reaction equation
C(=O)(O)[O-].[Na+].ClCC([O:10][C@@H:11]1[CH2:30][CH2:29][C@@:28]2([CH3:31])[C@@H:13]([CH2:14][CH2:15][C@@H:16]3[C@@H:27]2[C@@H:26]([O:32][C:33](=[O:36])[CH2:34][Cl:35])[CH2:25][C@@:24]2([CH3:37])[C@H:17]3[CH2:18][CH2:19][C@@H:20]2[C:21](=[O:23])[CH3:22])[CH2:12]1)=O>CO>[Cl:35][CH2:34][C:33]([O:32][C@H:26]1[CH2:25][C@@:24]2([CH3:37])[C@@H:17]([CH2:18][CH2:19][C@@H:20]2[C:21](=[O:23])[CH3:22])[C@H:16]2[C@H:27]1[C@:28]1([CH3:31])[C@@H:13]([CH2:14][CH2:15]2)[CH2:12][C@H:11]([OH:10])[CH2:30][CH2:29]1)=[O:36]

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 867368843alpha,11beta-Bischloroacetoxy-5alpha-pregnan-20-one

Product 1

HCID 8673686911beta-Chloroacetoxy-3alpha-hydroxy-5alpha-pregnan-20-oneYield 78.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Saturated sodium bicarbonate solution (200 ml) was added slowly to a stirred refluxing solution of 3α,11β-bischloroacetoxy-5α-pregnan-20-one (89 g) in methanol (1800 ml). After about 3.5 hours the mixture was evaporated to half its volume, water was added and the steroid was extracted with ethyl acetate. The washed and dried extract was evaporated in vacuo, the residue was filtered through a short column of silica in ethyl acetate-petroleum ether (1:1) and crystallised from ethyl acetate-petroleum ether to afford title compound (59 g), m.p. 83°-86°, [α]D +101° (c 1.0).

Workup

  1. customAfter about 3.5 hours the mixture was evaporated to half its volume, water
  2. additionwas added
  3. extractionthe steroid was extracted with ethyl acetate
  4. washThe washed
  5. customdried
  6. extractionextract
  7. customwas evaporated in vacuo
  8. filtrationthe residue was filtered through a short column of silica in ethyl acetate-petroleum ether (1:1)
  9. customcrystallised from ethyl acetate-petroleum ether

Sources & evidence

ORD record
ord-a689ca136b554e0e8cbda14410413f79
Source dataset
uspto-grants-1980_03
Patent number
US04192871

Reaction notes

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