Sodium borohydride → Methyl 3alpha,11beta-dihydroxy-5alpha-androstane-17beta-carboxylate

HRID 1701444Notes

Reaction equation

HRID 1701444 reaction equation
[BH4-].[Na+].[OH:3][C@@H:4]1[CH2:21][CH2:20][C@@:19]2([CH3:22])[C@@H:6]([CH2:7][CH2:8][C@@H:9]3[C@@H:18]2[C:17](=[O:23])[CH2:16][C@@:14]2([CH3:15])[C@H:10]3[CH2:11][CH2:12][C@@H:13]2[C:24]([O:26][CH3:27])=[O:25])[CH2:5]1>O.CO>[OH:3][C@@H:4]1[CH2:21][CH2:20][C@@:19]2([CH3:22])[C@@H:6]([CH2:7][CH2:8][C@@H:9]3[C@@H:18]2[C@@H:17]([OH:23])[CH2:16][C@@:14]2([CH3:15])[C@H:10]3[CH2:11][CH2:12][C@@H:13]2[C:24]([O:26][CH3:27])=[O:25])[CH2:5]1

Participants

5

Reactant 2

HCID 4311764Sodium borohydride2×HCID 705861023alpha-Hydroxy-17beta-methoxycarbonyl-5alpha-androstan-11-one

Product 1

HCID 70583998Methyl 3alpha,11beta-dihydroxy-5alpha-androstane-17beta-carboxylateYield 64%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

Sodium borohydride (1.24 g) in water (7 ml) was added to a solution of methyl 3α-hydroxy-11-oxo-5α-androstane-17β-carboxylate (2.58 g) in methanol (60 ml) and the mixture refluxed for 30 minutes. A further portion of sodium borohydride (200 mg) in a little water was added and refluxing continued for 10 minutes more. Most of the solvent was removed in vacuo and, after cooling, the crystalline product was collected by filtration. Recrystallization from aqueous methanol afforded title compound (1.662 g),

Workup

  1. temperaturethe mixture refluxed for 30 minutes
  2. temperaturerefluxing
  3. customMost of the solvent was removed in vacuo
  4. temperatureafter cooling
  5. filtrationthe crystalline product was collected by filtration
  6. customRecrystallization from aqueous methanol

Sources & evidence

ORD record
ord-6376352dd74d4b18802333614636161f
Source dataset
uspto-grants-1980_03
Patent number
US04192871

Reaction notes

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