Pyridine → N-[3-({[tert-Butyl(dimethyl)silyl]oxy}methyl)-4-chlorobenzyl]-N-methylacetamide
Reaction equation
[Si:1]([O:8][CH2:9][C:10]1[CH:11]=[C:12]([CH:16]=[CH:17][C:18]=1[Cl:19])[CH2:13]CN)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[C:20]([O:23]C(=O)C)(=O)[CH3:21].[N:27]1C=CC=C[CH:28]=1>>[Si:1]([O:8][CH2:9][C:10]1[CH:11]=[C:12]([CH:16]=[CH:17][C:18]=1[Cl:19])[CH2:13][N:27]([CH3:28])[C:20](=[O:23])[CH3:21])([C:4]([CH3:5])([CH3:6])[CH3:7])([CH3:2])[CH3:3]Participants
4
Procedure
To a solution of [3-({[tert-butyl(dimethyl)silyl]oxy}methyl)-4-chlorobenzyl]methylamine from the previous step (1 eq.) in pyridine (0.09 M) was added acetic anhydride (1.1 eq.) The resulting reaction mixture was stirred at RT for 3 h. After quenching the reaction with H2O, the mixture was extracted with EtOAc. The combined organic extracts were washed with 10% aq. HCl, sat. aq. NaHCO3, and brine. Drying over Na2SO4, filtration and concentration of the filtrate in vacuo afforded the crude product as a brown oil. Purification by way of flash chromatography (SiO2, 7:3 (v/v) Hex:EtOAc→EtOAc) afforded the title compound as a pale yellow oil.
Workup
- customThe resulting reaction mixture
- customAfter quenching
- customthe reaction with H2O
- extractionthe mixture was extracted with EtOAc
- washThe combined organic extracts were washed with 10% aq. HCl, sat. aq. NaHCO3, and brine
- dry with materialDrying over Na2SO4, filtration and concentration of the filtrate in vacuo
- customafforded the crude product as a brown oil
- customPurification by way of flash chromatography (SiO2, 7:3 (v/v) Hex:EtOAc→EtOAc)
Sources & evidence
- ORD record
- ord-2d09acda191744bc82593a596c41eaa6
- Source dataset
- uspto-grants-2011_11
- Patent number
- US08063105B2
Reaction notes
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