Triphenylphosphine → Ammonia

Participants

Reaction Steps

To a solution of 3-{(1S,5R)-1-[4-(trifluoromethyl)phenyl]-3-azabicyclo[3.1.0]hex-3-yl}-1-propanol (Prep5, 51 mg), 3-(phenylcarbonyl)-2,4(1H,3H)-pyrimidinedione (39 mg, prepared according to the procedure reported in J. Chem. Soc., Perkin Trans. 1, 2827 (1998)) and PPh3 (140 mg) in dry dioxane at 110° C., DEAD (40% solution in toluene, 0.243 mL) was added dropwise. After 3 hours the mixture was concentrated under reduced pressure. The crude product was purified by a silica SPE cartridge (10 g) eluting with DCM/MeOH from 100/0 to 95/5 followed by a SCX cartridge (eluting with MeOH and then NH3 0.3M in methanol) to give the title compound as a colourless oil (35 mg).

Provenance & Evidence