Carbon tetrabromide → 2-[N,N-bis(tert-Butoxycarbonyl)amino]-5-bromomethyl-3-methyl-pyridin

Participants

Reaction Steps

Triphenylphosphine (7.43 g, 28.3 mmol) and CBr4 (9.49 g, 28.6 mmol) was added to a solution of 2-[N,N-bis(tert-butoxycarbonyl)amino]-5-hydroxymethyl-3-methylpyridin (8.00 g, 23.6 mmol) in dichloromethane (220 mL) at 0° C. The reaction mixture was stirred for 3 h and was then concentrated under reduced pressure. Flash chromatography (hexane/EtOAc, 80:20) gave 5-bromomethyl-2-[N,N-bis(tert-butoxycarbonyl)amino]-3-methylpyridin (8.0 g,77%).

Provenance & Evidence