Allopregnanolone → Allopregnane-3alpha,20beta-diol

HRID 232808Notes

Reaction equation

HRID 232808 reaction equation
[OH:1][C@@H:2]1[CH2:21][CH2:20][C@@:19]2([CH3:22])[C@@H:4]([CH2:5][CH2:6][C@@H:7]3[C@@H:18]2[CH2:17][CH2:16][C@@:15]2([CH3:23])[C@H:8]3[CH2:9][CH2:10][C@@H:11]2[C:12](=[O:14])[CH3:13])[CH2:3]1.[BH4-].[Na+]>CO.ClCCl>[OH:1][C@@H:2]1[CH2:21][CH2:20][C@@:19]2([CH3:22])[C@@H:4]([CH2:5][CH2:6][C@@H:7]3[C@@H:18]2[CH2:17][CH2:16][C@@:15]2([CH3:23])[C@H:8]3[CH2:9][CH2:10][C@@H:11]2[C@H:12]([OH:14])[CH3:13])[CH2:3]1

Participants

5

Reactant 2

HCID 92786AllopregnanoloneHCID 4311764Sodium borohydride

Product 1

HCID 22868516Allopregnane-3alpha,20beta-diol

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 3α-hydroxy-5α-pregnan-20-one (3.2g, 318.5 g/m, 10 mmol) in 160 mL of methanol and 30 mL of dichloromethane at room temperature was slowly added sodium borohydride (3.3 g, 37.8 g/m, 87 mmol) over a period of 2 h. The mixture was stirred for an additional hour and then poured into ice cold water (700 mL) and extracted three times with ether. The combined organic phase was washed several times with water, dried over magnesium sulfate and concentrated to a white solid (2.35 g, 320.5 g/m, 7.3 mmol, 73%).

Workup

  1. customat room temperature
  2. customof 2 h
  3. extractionextracted three times with ether
  4. washThe combined organic phase was washed several times with water
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated to a white solid (2.35 g, 320.5 g/m, 7.3 mmol, 73%)

Sources & evidence

ORD record
ord-736c3ce8e07940ef91b73f6ee677b435
Source dataset
uspto-grants-1997_01
Patent number
US05591733

Reaction notes

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