4-(4-Fluoro-benzyl)-piperidine → HCID 54284239, compound

Participants

Reaction Steps

A solution of (+/−)-N-(t-butoxycarbonyl)-3-piperidinecarboxaldehyde (521 mg, 2.45 mmol) and 4-(4-flourophenylmethyl)piperidine (315 mg, 1.63 mmol) in dry CH2Cl2 (20 mL) was stirred for 15 min when sodium triacetoxyborohydride (691 mg, 3.26 mmol, Aldrich) was added. The reaction was stirred for 4 h and then quenched with 10% NaOH (10 mL) and CH2Cl2 (100 mL). The organic layer was separated, dried over MgSO4, and conc. in vacuo to a pale yellow oil. The oil was purified by radial chromatography (SiO2, CH2Cl2:MeOH, 98:2) to yield 580 mg the product as a colorless oil. MS (ESI) 391 (M+H).

Provenance & Evidence