Sodium borohydride → Obeticholic Acid

HRID 591872

Reaction equation

HRID 591872 reaction equation
[OH:1][C@@H:2]1[CH2:25][CH2:24][C@@:23]2([CH3:26])[C@H:4]([C@@H:5]([CH2:29][CH3:30])[C:6](=[O:28])[C@@H:7]3[C@@H:22]2[CH2:21][CH2:20][C@@:19]2([CH3:27])[C@H:8]3[CH2:9][CH2:10][C@@H:11]2[C@H:12]([CH3:18])[CH2:13][CH2:14][C:15]([OH:17])=[O:16])[CH2:3]1.[BH4-].[Na+]>>[CH3:30][CH2:29][C@H:5]1[C@@H:6]([OH:28])[C@@H:7]2[C@H:22]([CH2:21][CH2:20][C@:19]3([CH3:27])[C@@H:11]([C@@H:12]([CH2:13][CH2:14][C:15]([OH:17])=[O:16])[CH3:18])[CH2:10][CH2:9][C@H:8]32)[C@:23]2([CH3:26])[C@H:4]1[CH2:3][C@H:2]([OH:1])[CH2:25][CH2:24]2

Participants

3

Reactant 2

HCID 4311764Sodium borohydrideHCID 67102585(R)-4-((3R,5S,6R,8S,9S,10S,13R,14S,17R)-6-ethyl-3-hydroxy-10,13-dimethyl-7-oxohexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)pentanoic acid

Product 1

HCID 447715Obeticholic Acid

Procedure

reacting 3α-hydroxy-6α-ethyl-7-keto-5β-cholan-24-oic acid (6) with NaBH4 to form crystalline obeticholic acid, and

Sources & evidence

ORD record
ord-5b9101ff716f47e1b97a9ecfcefdcb94
Source dataset
uspto-grants-2016_01
Patent number
US09238673B2

Linked notes

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