tert-butyl N-[(2S)-4-methyl-1-oxopentan-2-yl]carbamate → (s)-[1-(2-Amino-4-methyl-pentyl)-piperidin-4-yl]-(4-benzyloxy-phenyl)-(3-methyl-but-2-enyl)-amine

Participants

Reaction Conditions

Reaction Steps

Boc-L-leucinal (0.78 g, 3.64 mmol) was treated with a solution of (4-Benzyloxy-phenyl)-(3-methyl-but-2-enyl)-piperidin-4-yl-amine (1.28 g, 3.64 mmol) in CH2Cl2 (36 mL), stirred 15 minutes, cooled to 0° C., and treated with NaBH(OAc)3 (1.16 g, 5.46 mmol). The reaction was allowed to warm to RT as ice melted and stir 4 hours. The reaction was diluted with EtOAc (200 mL), washed with saturated bicarbonate solution, and brine, dried over Na2SO4, and concentrated. The residue was chromatographed on silica gel eluting with 8% MeOH/CH2Cl2 to give 1.15 g (57%) of the desired product (Id).

Provenance & Evidence