Sodium borohydride → HCID 68781188, compound

HRID 1182889Notes

Reaction equation

HRID 1182889 reaction equation
[C:1]([O:4][C@@H:5]1[C:22](=[O:23])[CH2:21][CH2:20][C@@:19]2([CH3:24])[C:6]1=[CH:7][CH2:8][C@@H:9]1[C@@H:18]2[CH2:17][CH2:16][C@@:14]2([CH3:15])[C@H:10]1[CH2:11][CH2:12][C:13]2=[O:25])(=[O:3])[CH3:2].[BH4-].[Na+]>CO>[C:1]([O:4][C@@H:5]1[CH:22]([OH:23])[CH2:21][CH2:20][C@@:19]2([CH3:24])[C:6]1=[CH:7][CH2:8][C@@H:9]1[C@@H:18]2[CH2:17][CH2:16][C@@:14]2([CH3:15])[C@H:10]1[CH2:11][CH2:12][C@@H:13]2[OH:25])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 68729360HCID 68729360, compound

Product 1

HCID 68781188HCID 68781188, compoundYield 98.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a suspension of 4α-acetoxyandrost-5-ene-3,17-dione (600 mg) in MeOH (20 ml) at 0° C., NaBH4 (70 mg) was added. The mixture was warmed and stirred for 1 h at RT. The solution was neutralized by addition of 5% NaH2PO4 and the organic solvent was evaporated. The residue was taken up in H2O and extracted with DCM. The combined organic extracts were washed with brine, dried over Na2SO4 and evaporated to dryness. The resulting 4α-acetoxyandrost-5-ene-3,17β-diol (600 mg) was obtained as a 3α:3β mixture and used without purification in the next step.

Workup

  1. temperatureThe mixture was warmed
  2. customthe organic solvent was evaporated
  3. extractionextracted with DCM
  4. washThe combined organic extracts were washed with brine
  5. dry with materialdried over Na2SO4
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-798e3e137d3143a28ed0bdcf90e511fa
Source dataset
uspto-grants-2014_03
Patent number
US08664210B2

Reaction notes

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