Pyridine → HCID 23302078, compound

Participants

Reaction Steps

Cool a mixture of 4-[N-(t-butoxycarbonyl)-N-[(phenyl)methyl]-amino]butan-1-ol (21.8 g, 0.078 mol), methylene chloride (250 mL) and pyridine (9.7 mL). Add mesylchloride (6.65 mL, 0.086 mol) in methylene chloride (6.6 mL) dropwise to the reaction with stirring. After addition is complete, allow the reaction to warm to room temperature and stir for an additional 2 hours. Pour the reaction into methylene chloride (200 mL), rinse with 0.5 N hydrochloric acid (500 mL), saturated sodium bicarbonate (500 mL), dry over anhydrous magnesium sulfate, filter and concentrate under vacuum. Purify the residue by flash chromatography (25% ethyl acetate/hexane, silica gel) to provide 4-[N-(t-butoxycarbonyl)-N-[(phenyl)methyl]-amino]-1-methansulfonyl butane (10.7 g), Rf =0.36 eluting with 25% ethyl acetate/hexane.

Provenance & Evidence