Sodium borohydride → 16beta-Methyl-5alpha-androstan-17alpha-ol

HRID 1199157Notes

Reaction equation

HRID 1199157 reaction equation
[CH3:1][C@H:2]1[CH2:7][C@H:6]2[C@H:8]3[C@H:18]([CH2:19][CH2:20][C@:4]2([CH3:5])[C:3]1=[O:21])[C@:16]1([CH3:17])[C:11]([CH2:12][CH2:13][CH2:14][CH2:15]1)=[CH:10][CH2:9]3.[BH4-].[Na+]>[Pd]>[CH3:1][C@H:2]1[CH2:7][C@H:6]2[C@H:8]3[C@H:18]([CH2:19][CH2:20][C@:4]2([CH3:5])[C@@H:3]1[OH:21])[C@:16]1([CH3:17])[C@H:11]([CH2:12][CH2:13][CH2:14][CH2:15]1)[CH2:10][CH2:9]3.[CH3:1][C@H:2]1[CH2:7][C@H:6]2[C@H:8]3[C@H:18]([CH2:19][CH2:20][C@:4]2([CH3:5])[C@H:3]1[OH:21])[C@:16]1([CH3:17])[C@H:11]([CH2:12][CH2:13][CH2:14][CH2:15]1)[CH2:10][CH2:9]3

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 5434781216beta-Methly-5-androsten-17-one

Product 2

HCID 7035954116beta-Methyl-5alpha-androstan-17alpha-olHCID 7035962216beta-Methyl-5alpha-androstan-17beta-ol

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

Similarly, catalytic hydrogenation over 5% palladium on carbon of the 16β-methyl-5-androsten-17-one produced in Example 5 followed by treatment with sodium borohydride affords 16β-methyl-5α-androstan-17α-ol and 16β-methyl-5α-androstan-17β-ol.

Sources & evidence

ORD record
ord-500a83e2dbb340e08c7ce3b5cbee8edc
Source dataset
uspto-grants-1990_02
Patent number
US04898694

Reaction notes

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