Triphenylphosphine → HCID 69254250, compound

Participants

Reaction Conditions

Reaction Steps

A stirring solution of 3-[(2-chloro-3-trifluoromethyl-benzyl)-(2,2-diphenyl-ethyl)-amino]-propan-1-ol (282 mg, 0.38 mmol) in toluene (25 mL) was treated with 3-morpholin-4-yl-phenol (75 mg, 0.42 mmol). Polymer bound triphenylphosphine (224 mg, 0.67 mmol, 3 mmol/g, Fluka Chemie) was then added, and the mixture was stirred for 15 minutes. The reaction mixture was then cooled to 0° C. and diisopropylazodicarboxylate (127 mg, 0.63 mmol) was added in a dropwise fashion. After stirring at room temperature overnight, the crude reaction mixture was filtered and the solid washed with toluene (25 mL). The filtrate was concentrated in vacuo. Purification by preparative HPLC (YMC 75×30 mm, 25 ml/min, 85-100% CH3CN over) led to the isolation of the morpholine product. The free base was treated with 1 M HCl in Et2O (0.1 ml) and the mixture was concentrated in vacuo to afford the title compound as a solid, 104 mg (41%). MS(ES) m/e 609.4 (M+).

Provenance & Evidence