Toluene → N-[(R)-2-[(1-Isopropylpiperidin-4-ylmethyl)amino]-1-phenyl-ethyl]carbamic acid tert-butyl ester

Participants

Reaction Conditions

Reaction Steps

To a solution of N-[(R)-2-[(1-isopropylpiperidin-4-yl-methyl) amino]-1-phenyl-2-oxoethyl]carbamic acid tert-butyl ester (1.0 g, 2.6 mmol) in 15 mL of THF was added 65 wt % sodium bis(2-methoxyethoxy)aluminum hydride in toluene (2.4 mL, 7.7 mmol). The reaction mixture was heated at reflux for 3 h after which time the mixture was cooled to 0° C. and the reaction was quenched by the slow addition of a saturated solution of Rochelle's salt. The product was extracted into EtOAc; and the combined extracts were dried over sodium sulfate, filtered, and concentrated to afford, after purification (SiO2: 0 to 30% isopropylamine in 1:1 hexane:EtOAc), 0.9 g (94%) of the title compound.

Provenance & Evidence