Tributylphosphine → Ethyl 3-{3-chloro-5-(methyloxy)-4-[((1S)-1-{6-[4-(trifluoromethyl)phenyl]-2-pyridinyl}pentyl)oxy]phenyl}propanoate

Participants

Reaction Conditions

Reaction Steps

To a stirring solution of (1R)-1-{6-[4-(trifluoromethyl)phenyl]-2-pyridinyl}-1-pentanol (66 mg, 0.21 mmol) and ethyl 3-[3-chloro-4-hydroxy-5-(methyloxy)phenyl]propanoate (78 mg, 0.30 mmol) in THF (4 mL) at 0° C. under nitrogen was added ADDP (100 mg, 0.40 mmol) followed by nBu3P (0.10 mL, 0.40 mmol). The resulting mixture was then stirred at 0° C. with slow warming to ambient temperature over 19 h and then reduced under vacuum (Genevac). The residue was then purified by SPE (silica, 10 g cartridge) with a pad of celite on the top, eluting with cyclohexane:EtOAc (gradient 100:1 to 3:1) to afford the title compound (118 mg).

Provenance & Evidence