[4-(tert-Butyl-dimethyl-silanyloxy)-2-methyl-phenyl]-methyl-carbamic acid benzyl ester → 4-[(tert-butyldimethylsilyl)oxy]-N,2-dimethylaniline

HRID 2261811Notes

Reaction equation

HRID 2261811 reaction equation
C(O[C:9](=O)[N:10]([C:12]1[CH:17]=[CH:16][C:15]([O:18][Si:19]([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:21])[CH3:20])=[CH:14][C:13]=1[CH3:26])C)C1C=CC=CC=1>[Pd].CO>[C:22]([Si:19]([CH3:21])([CH3:20])[O:18][C:15]1[CH:16]=[CH:17][C:12]([NH:10][CH3:9])=[C:13]([CH3:26])[CH:14]=1)([CH3:25])([CH3:24])[CH3:23]

Participants

4

Reactant 1

HCID 66704094[4-(tert-Butyl-dimethyl-silanyloxy)-2-methyl-phenyl]-methyl-carbamic acid benzyl ester

Product 1

HCID 667041204-[(tert-butyldimethylsilyl)oxy]-N,2-dimethylanilineYield 81.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

The mixture of [4-(tert-butyl-dimethyl-silanyloxy)-2-methyl-phenyl]-methyl-carbamic acid benzyl ester (14.0 g, 36.0 mmol) and palladium on carbon (10 wt %, 0.5 g) in methanol (100.0 mL) is stirred under an atmosphere of hydrogen at room temperature overnight. The reaction mixture is filtered and the filtrate is concentrated under reduced pressure to a residue. The residue is purified by flash chromatography to afford the title compound as oil (7.4 g, 81%). LC-ES/MS m/e 252.3 (M+1).

Workup

  1. filtrationThe reaction mixture is filtered
  2. concentrationthe filtrate is concentrated under reduced pressure to a residue
  3. customThe residue is purified by flash chromatography

Sources & evidence

ORD record
ord-c87de1fe377c4e8e9c4fc96d4cacaa25
Source dataset
uspto-grants-2010_12
Patent number
US07846960B2

Reaction notes

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