Sodium borohydride → HCID 68781188, compound
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
Product 1
Reagents, catalysts & solvents 1
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.