Sodium Bicarbonate → HCID 59178549, compound

Participants

Reaction Steps

To a mixture of 868 mg of (1R)-1-(1-naphthyl)ethaneamine, 0.073 mL of acetic acid, 1.29 g of sodium triacetoxyborohydride, and 75 mL of 1,2-dichloroethane was added dropwise a solution of 1.446 g of a crude rel-(3R,4S)-4-phenyl-1-(trifluoroacetyl)piperidine-3-carbaldehyde in 25 mL of 1,2-dichloroethane at room temperature, followed by stirring overnight. To the reaction mixture was added a saturated aqueous sodium hydrogen carbonate solution, followed by vigorously stirring for 10 minutes, and then extracting with chloroform, and the organic layer was dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (chloroform-methanol) to obtain 1.84 g of (1R)-1-(1-naphthyl)-N-{[4-phenyl-1-(trifluoroacetyl)piperidin-3-yl]methyl}ethaneamine as a colorless foamy substance.

Provenance & Evidence