Sodium borohydride → HCID 69762612, compound

HRID 1448018Notes

Reaction equation

HRID 1448018 reaction equation
[OH:1][C@@H:2]1[CH2:27][CH2:26][C@@:25]2([CH3:28])[C@H:4]([C@@H:5]([OH:30])[CH2:6][C@@H:7]3[C@@H:24]2[CH2:23][CH2:22][C@@:21]2([CH3:29])[C@H:8]3[CH2:9][CH2:10][C@@H:11]2[C@H:12]([CH3:20])[CH2:13][CH2:14][C:15](=[O:19])[CH:16]([CH3:18])[CH3:17])[CH2:3]1.[BH4-].[Na+]>CO>[OH:1][C@@H:2]1[CH2:27][CH2:26][C@@:25]2([CH3:28])[C@H:4]([C@@H:5]([OH:30])[CH2:6][C@@H:7]3[C@@H:24]2[CH2:23][CH2:22][C@@:21]2([CH3:29])[C@H:8]3[CH2:9][CH2:10][C@@H:11]2[C@H:12]([CH3:20])[CH2:13][CH2:14][CH:15]([OH:19])[CH:16]([CH3:18])[CH3:17])[CH2:3]1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 22809505HCID 22809505, compound

Product 1

HCID 69762612HCID 69762612, compoundYield 76.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To the solution of 3α,6α-dihydroxy-5β-cholestan-24-one (2.6 g) in methanol (200 ml) was added sodium borohydride (2 g) and stirred for one hour under cooling with ice. After decomposition of excess sodium borohydride with aqueous solution of acetic acid, the mixture was evaporated to reduce the volume to about 100 ml and the residue was extracted with ethyl acetate. The ethyl acetate layer was washed with water, dried over magnesium sulfate and evaporated to give 2.0 g of 3α,6α,24-trihydroxy-5β-cholestane having a melting point of 169°-173° C. after recrystallization from chloroform.

Workup

  1. temperatureunder cooling with ice
  2. customAfter decomposition of excess sodium borohydride with aqueous solution of acetic acid, the mixture was evaporated
  3. extractionthe residue was extracted with ethyl acetate
  4. washThe ethyl acetate layer was washed with water
  5. dry with materialdried over magnesium sulfate
  6. customevaporated

Sources & evidence

ORD record
ord-e814d2770dd64bf589673b56e027d362
Source dataset
uspto-grants-1979_12
Patent number
US04179452

Reaction notes

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