Triphenylphosphine → 3-{2-[4-(4-Chloro-3-methoxy-phenyl)-piperazin-1-yl]-2-oxo-ethyl}-6-[2-(tetrahydro-pyran-2-yloxy)-ethoxy]-3H-benzooxazol-2-one

Participants

Reaction Conditions

Reaction Steps

To a mixture of PPh3 (70 mg, 0.27 mmol, 1.1 eq), and DEAD (40 mg, 0.23 mmol, 1 eq) in THF (0.5 ml), was added 3-{2-[4-(4-chloro-3-methoxy-phenyl)-piperazin-1-yl]-2-oxo-ethyl}-6-hydroxy-3H-benzooxazol-2-one (54) (100 mg, 0.24 mmol, 1 eq) in THF (1 ml). The reaction mixture immediately turned clear and was heated to 85° C. 2-(Tetrahydro-pyran-2-yloxy)-ethanol (38.5 mg, 0.27 mmol, 1.1 eq), was then added to the reaction solution, and stirred for 3 hours at rt. The isolated crude product was purified with HPLC to provide 3-{2-[4-(4-chloro-3-methoxy-phenyl)-piperazin-1-yl]-2-oxo-ethyl}-6-[2-(tetrahydro-pyran-2-yloxy)-ethoxy]-3H-benzooxazol-2-one (55).

Provenance & Evidence