Water → 1-(2-Amino-5-{[tert-butyl(dimethyl)silyl]oxy}phenyl)pentan-1-one

HRID 1986459Notes

Reaction equation

[NH2:1][C:2]1[CH:13]=[CH:12][C:11]([O:14][Si:15]([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:17])[CH3:16])=[CH:10][C:3]=1[C:4](N(OC)C)=[O:5].[CH2:22]([Li])[CH2:23][CH2:24][CH3:25].O>O1CCCC1.CCCCCC>[NH2:1][C:2]1[CH:13]=[CH:12][C:11]([O:14][Si:15]([C:18]([CH3:19])([CH3:20])[CH3:21])([CH3:16])[CH3:17])=[CH:10][C:3]=1[C:4](=[O:5])[CH2:22][CH2:23][CH2:24][CH3:25]

Participants

Conditions

Temperature: -78 °C

Procedure

To a solution of 2-amino-5-{[tert-butyl(dimethyl)silyl]oxy}-N-methoxy-N-methylbenzamide (4.97 g, 16.0 mmol) in tetrahydrofuran (50 ml) was added dropwise slowly 1.6 M solution (20 ml) of n-butyllithium in n-hexane at −78° C., and after the completion of the dropwise addition, the mixture was stirred at −78° C. for 30 min. The reaction mixture was poured into water and extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography to give 1-(2-amino-5-{[tert-butyl(dimethyl)silyl]oxy}phenyl)pentan-1-one (3.45 g, yield 70%) as a pale-yellow oil.

Workup

additionafter the completion of the dropwise addition
extractionextracted with ethyl acetate
washThe extract was washed with saturated brine
dry with materialdried over anhydrous magnesium sulfate
customThe solvent was evaporated under reduced pressure
customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record: ord-ab184993a0bc4d648ce3b229335cbac7
Source dataset: uspto-grants-2009_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07547710B2

Reaction notes

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