Carbon tetrabromide → 2-[N,N-bis(tert-butoxycarbonyl)amino]-5-bromomethyl-4-methyl-pyridin

Participants

Reaction Steps

Triphenylphosphine (4.69 g, 17.9 mmol) and CBr4 (4.89 g, 14.8 mmol) was added to a solution of 2-[N,N-bis(tert-butoxycarbonyl)amino]-5-hydroxymethyl-4-methylpyridin (5.00 g, 22.0 mmol) in dichloromethane (130 mL) at 0° C. The reaction mixture was stirred for 3 h and was then diluted with dichloromethane. The organic phase was washed with water, dried and concentrated under reduced pressure. Flash chromatography (hexane/EtOAc, 80:20) gave 5-bromomethyl-2-[N,N-bis(tert-butoxycarbonyl)amino]-4-methylpyridin (5.35 g, 90%).

Provenance & Evidence