Trifluoroacetic acid → HCID 59201442, compound

Participants

Reaction Steps

A 100 mL round bottom flask was charged with 0.092 g of TFA salt of (3S)-tert-butyl 3-(4-amino-1-(3-fluorophenyl)butyl)piperidine-1-carboxylate, 0.152 g of DMAP, 10 mL of CH2Cl2, and 2 mL of DIPEA. The mixture was cooled with an ice bath and then a solution of methyl chloroformate (0.280 g) in CH2Cl2 (3 mL) was added. The reaction mixture was allowed to slowly warm to rt while stirring overnight. After the reaction mixture was evaporated under reduced pressure, the crude product was purified by reversed-phase HPLC (Phenomenex® Luna 5μ C18(2) 100 A, 250×21.20 mm, 5 micron, 70%→90% CH3CN/H2O, 0.1% CF3COOH over 8 min and then 90% CH3CN/H2O, 0.1% CF3COOH over 2 min, flow rate 25 mL/min) to afford 0.0306 g (38%) of (3S)-tert-butyl 3-(1-(3-fluorophenyl)-4-(methoxycarbonylamino)butyl)piperidine-1-carboxylate. Isomer 1 and 2, MS ESI +ve m/z 431 (MNa+), 409 (MH+), tR=1.91, 1.98 min in 3 min chromatography.

Provenance & Evidence