Pyridine → N-[3-({[tert-Butyl(dimethyl)silyl]oxy}methyl)-4-chlorobenzyl]-N-methylacetamide

Participants

Reaction Steps

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.

Provenance & Evidence