Methanol → HCID 67986524, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 0.500 mL (4.03 mmol) of 2-fluoroacetophenone and 0.50 g (2.68 mmol) of tert-butyl piperazine-1-carboxylate in 1.5 mL of anhydrous tetrahydrofuran under an atmosphere of nitrogen was added 2.50 mL (8.60 mmol) of titanium(IV) isopropoxide. The resulting mixture was heated to 80° C. for 12 h then cooled to 0° C. Next, 1.8 g (8.6 mmol) of solid sodium triacetoxyborohydride was added in one portion and the resulting solution was stirred with gradual warming to ambient temperature over 4 h. The reaction mixture was quenched with 1.0 mL (25 mmol) of methanol and then diluted with dichloromethane and a saturated aqueous sodium hydrogen carbonate solution. The mixture was filtered through a pad of Celite® and the layers separated. The aqueous phase was extracted with dichloromethane and the combined organic layers were washed with brine, dried over magnesium sulfate filtered and evaporated to dryness in vacuo. The crude residue was purified by silica gel chromatography eluting with a 0-100% ethyl acetate in hexanes gradient to afford the title compound as colorless oil (0.048 g, 58%). LC-MS: m/z (ES) 309.2 (MH)+

Provenance & Evidence