Methanol → Triphenylphosphine Oxide

Participants

Reaction Steps

To a solution of the N-tert-butoxycarbonyl phenyl alaninol (1.42 mmol) and triphenylphosphine (2 equiv) in DMF, N-bromosuccinimide (2 equiv) was slowly added. The reaction was warmed to 50° for 15 min and then cooled to 20°. Methanol (0.5 mL) was added to destroy the excess reagent. After 5 min, ether was added, and the ether layer was washed with water, saturated sodium carbonate, and saturated NaCl and then evaporated to a solid under high vacuum. The product was extracted twice into hexane, leaving a residue of triphenylphosphine oxide. After evaporation of the solvent, the residue was again triturated with hexane to afford the 1-Bromo-2-(tert-butoxycarbonyl)amino-3-phenyl propane:

Provenance & Evidence