Red-Al → (R)-tert-butyl 3-((R)-(2-aminoethoxy)(3-chlorophenyl)methyl)piperidine-1-carboxylate

Participants

Reaction Steps

To a solution of (R)-tert-butyl 3-((R)-(2-amino-2-oxoethoxy)(3-chlorophenyl)methyl)piperidine-1-carboxylate (902 mg, 2.36 mmol) in anhydrous toluene (30 mL) at 0° C. was added Red-Al® (65% solution in toluene, 1.4 mL, 7.07 mmol) slowly over 10 min. After the addition, the solution was stirred overnight at room temperature. The reaction was cooled to 0° C. and quenched with Na2SO4.10H2O. The resulting mixture was stirred for 2-3 h, filtered through Celite®, and washed with THF (200 mL). The filtrate was dried and concentrated to give crude product (R)-tert-butyl 3-((R)-(2-aminoethoxy)(3-chlorophenyl)methyl)piperidine-1-carboxylate (776 mg, 89%). MS ESI +ve m/z 369 (M+H)+.

Provenance & Evidence