Methanol → [2-(Benzyloxy)-4-({[tert-butyl(dimethyl)silyl]oxy}methyl)-6-methylpyridin-3-yl]methanol

HRID 577444Notes

Reaction equation

HRID 577444 reaction equation
[CH2:1]([O:8][C:9]1[C:14]([C:15]#N)=[C:13]([CH2:17][O:18][Si:19]([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:21])[CH3:20])[CH:12]=[C:11]([CH3:26])[N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+].C[OH:30]>>[CH2:1]([O:8][C:9]1[C:14]([CH2:15][OH:30])=[C:13]([CH2:17][O:18][Si:19]([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:21])[CH3:20])[CH:12]=[C:11]([CH3:26])[N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 4311764Sodium borohydrideHCID 867236812-(Benzyloxy)-4-({[tert-butyl(dimethyl)silyl]oxy}methyl)-6-methylpyridine-3-carbonitrile

Product 1

HCID 86723682[2-(Benzyloxy)-4-({[tert-butyl(dimethyl)silyl]oxy}methyl)-6-methylpyridin-3-yl]methanolYield 14%

Procedure

To a 0° C. solution of 2-(benzyloxy)-4-({[tert-butyl(dimethyl)silyl]oxy}methyl)-6-methylpyridine-3-carbonitrile (Cpd I, 1.0 g, 2.8 mmol) in MeOH (5 mL) was added NaBH4 (81 mg, 2.1 mmol). The reaction mixture was allowed to stir at room temperature for 24 hours. The reaction mixture was concentrated under vacuum to give [2-(benzyloxy)-4-({[tert-butyl(dimethyl)silyl]oxy}methyl)-6-methylpyridin-3-yl]methanol (Cpd J, 147 mg, 14%) as a solid.

Workup

  1. concentrationThe reaction mixture was concentrated under vacuum

Sources & evidence

ORD record
ord-d750a8ffc296451489403210480eb1ac
Source dataset
uspto-grants-2015_05
Patent number
US09040515B2

Reaction notes

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