Sodium borohydride → HCID 69411552, compound

HRID 1764941Notes

Reaction equation

HRID 1764941 reaction equation
[CH3:1][O:2][C:3](=[O:30])[CH2:4][CH2:5][C@H:6]([C@@H:8]1[C@:25]2([CH3:26])[C@H:11]([C@H:12]3[C@H:22]([CH2:23][CH2:24]2)[C@:20]2([CH3:21])[C:15]([C:16]([CH3:29])([CH3:28])[C:17](=[O:27])[CH2:18][CH2:19]2)=[CH:14][CH2:13]3)[CH2:10][CH2:9]1)[CH3:7].[BH4-].[Na+]>CO>[CH3:1][O:2][C:3](=[O:30])[CH2:4][CH2:5][C@H:6]([C@@H:8]1[C@:25]2([CH3:26])[C@H:11]([C@H:12]3[C@H:22]([CH2:23][CH2:24]2)[C@:20]2([CH3:21])[C:15]([C:16]([CH3:29])([CH3:28])[C@@H:17]([OH:27])[CH2:18][CH2:19]2)=[CH:14][CH2:13]3)[CH2:10][CH2:9]1)[CH3:7]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 13915902HCID 13915902, compound

Product 1

HCID 69411552HCID 69411552, compoundYield 96.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

4,4-Dimethyl-3-oxochol-5-en-24-oic acid methyl ester (19.8 g) (G. Aranda et al., Tetrahedron 43 (1987), 4147) is reduced with sodium borohydride (9.9 g) in 1900 ml methanol at room temperature. The solution is stirred for 20 hours. After aqueous work-up, 3β-hydroxy-4,4-dimethylchol-5-en-24-oic acid methyl ester (19.2 g) is isolated. Melting point: 136-138° C. 1H-NMR (CDCl3, 400 MHz): δ=5.55 (1H, m); 3.67 (3H, s); 3.23 (1H, m).

Sources & evidence

ORD record
ord-834532d00a814010a913eb17e3ef7f0b
Source dataset
uspto-grants-2007_06
Patent number
USRE039678E1

Reaction notes

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