Sodium borohydride → 20,20-Ethylenedioxy-5alpha-pregn-2-en-11beta-ol

HRID 1701441Notes

Reaction equation

HRID 1701441 reaction equation
[CH2:1]1[CH2:26][O:25][C:3]([C@@H:5]2[C@:22]3([CH3:23])[C@H:8]([C@H:9]4[C@H:19]([C:20](=[O:24])[CH2:21]3)[C@:17]3([CH3:18])[C@H:12]([CH2:13][CH:14]=[CH:15][CH2:16]3)[CH2:11][CH2:10]4)[CH2:7][CH2:6]2)([CH3:4])[O:2]1.[BH4-].[Na+]>C(O)C.O>[CH2:26]1[CH2:1][O:2][C:3]([C@@H:5]2[C@:22]3([CH3:23])[C@H:8]([C@H:9]4[C@H:19]([C@@H:20]([OH:24])[CH2:21]3)[C@:17]3([CH3:18])[C@H:12]([CH2:13][CH:14]=[CH:15][CH2:16]3)[CH2:11][CH2:10]4)[CH2:7][CH2:6]2)([CH3:4])[O:25]1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 70583481HCID 70583481, compound

Product 1

HCID 7058411420,20-Ethylenedioxy-5alpha-pregn-2-en-11beta-olYield 96.8%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

20,20-Ethylenedioxy-5α-pregn-2-en-11-one (9.3 g) in hot ethanol (300 ml) was treated with sodium borohydride (5.5 g) in water (30 ml), and the mixture was refluxed on a steam bath for 1 1/2 hours, concentrated by evaporation to about 200 ml, the excess borohydride destroyed by the addition of glacial acetic acid (0.5 ml), and the mixture poured on to ice-water to give a white crystalline precipitate. The precipitate was filtered off, washed with water and dried in vacuo to give title compound (9.05 g), as colourless needles, m.p. 141°-145°, [α]D +64°.

Workup

  1. temperaturethe mixture was refluxed on a steam bath for 1 1/2 hours
  2. concentrationconcentrated by evaporation to about 200 ml
  3. customthe excess borohydride destroyed by the addition of glacial acetic acid (0.5 ml)
  4. additionthe mixture poured on to ice-water
  5. customto give a white crystalline precipitate
  6. filtrationThe precipitate was filtered off
  7. washwashed with water
  8. customdried in vacuo

Sources & evidence

ORD record
ord-41912f224f024c0a94f05ba6714c788f
Source dataset
uspto-grants-1980_03
Patent number
US04192871

Reaction notes

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