Aluminium lithium hydride → tert-Butyl 3-(aminomethyl)-3-fluoropiperidine-1-carboxylate

Participants

Reaction Steps

To a stirred and cooled (0° C.) suspension of lithium aluminium hydride (1.02 g, 26.8 mmol) in dry THF (50 mL) was added drop-wise a solution of tert-butyl 3-cyano-3-fluoropiperidine-1-carboxylate (5.50 g, 24.0 mmol) in dry THF (30 mL). The reaction was stirred at 0° C. for 1 hour then at room temperature for 3 hours. The mixture was quenched with water (1.0 mL) at 0° C., and stirred at room temperature for 20 minutes. Then 15% sodium hydroxide aqueous solution (2.0 mL) was added, and stirred at room temperature for 20 minutes. Finally, water (1.0 mL) was added, and stirred at room temperature for 20 minutes. The mixture was filtered through Celite pad washing with tetrahydrofuran (25 mL). The filtrate was concentrated to afford the title product as pale yellow oil 3.86 g. MS (m/z): 233 (M+H)+

Provenance & Evidence