Sodium borohydride → HCID 57079451, compound

HRID 1764978Notes

Reaction equation

[C:1]([C@:3]12[CH2:28][C:27](=[O:29])[CH2:26][CH2:25][C@:24]1([CH3:30])[C:23]1[CH2:22][CH2:21][C@@:20]3([CH3:31])[C@@H:7]([CH2:8][CH2:9][C@@H:10]3[C@H:11]([CH3:19])[CH2:12][CH:13]3[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]3)[C:6]=1[CH2:5][CH2:4]2)#[N:2].[BH4-].[Na+]>>[C:1]([C@:3]12[CH2:28][C@@H:27]([OH:29])[CH2:26][CH2:25][C@:24]1([CH3:30])[C:23]1[CH2:22][CH2:21][C@@:20]3([CH3:31])[C@@H:7]([CH2:8][CH2:9][C@@H:10]3[C@H:11]([CH3:19])[CH2:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[C:6]=1[CH2:5][CH2:4]2)#[N:2].[C:1]([C@:3]12[CH2:28][C@H:27]([OH:29])[CH2:26][CH2:25][C@:24]1([CH3:30])[C:23]1[CH2:22][CH2:21][C@@:20]3([CH3:31])[C@@H:7]([CH2:8][CH2:9][C@@H:10]3[C@H:11]([CH3:19])[CH2:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[C:6]=1[CH2:5][CH2:4]2)#[N:2]

Participants

Reactant 2

HCID 4311764Sodium borohydride

HCID 57191327HCID 57191327, compound

Product 2

HCID 57079451HCID 57079451, compound

HCID 69410706HCID 69410706, compound

Procedure

152 mg (20R)-5-cyano-21-cyclohexyl-20-methyl-5α-pregn-8-en-3-one were treated with 50 mg sodium borohydride as described in example 58b. After column chromatography 36 mg (20R)-5-cyano-21-phenyl-20-methyl-5α-pregn-8-en-3β-ol and 46 mg (20R)-5-cyano-21-phenyl-20-methyl-5α-pregn-8-en-3α-ol were isolated.

Sources & evidence

ORD record: ord-9c390a115e19476aab08175dd9bb41e2
Source dataset: uspto-grants-2007_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: USRE039678E1

Reaction notes

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