Sodium Bicarbonate → Methyl1-Boc-4-[[(R)-1-phenylethyl]amino]piperidine-3-carboxylate

Participants

Reaction Conditions

Reaction Steps

A solution of 4-(1-phenyl-ethyl amino)-5,6-dihydro-2H-pyridine-1,3-dicarboxylic acid 1-tert-butyl ester 3-methyl ester (4 g, 11.1 mmol) in acetic acid-acetonitrile (1:1, 80 mL) was treated with sodium triacetoxyborohydride (2.59 g, 12.2 mmol), and stirred for 5 h at 0° C. The reaction was cooled to 0° C. and neutralized with saturated aqueous sodium bicarbonate (5 mL). The organic layer was washed with brine (3×20 mL), then dried over MgSO4, filtered and concentrated to obtain a crude oil (3.6 g). The crude product was purified by Biotage Flash 40S chromatography, eluting with 1:1 ethyl acetate-hexanes, to provide 4-(1-phenyl-ethylamino)-piperidine-1,3-dicarboxylic acid 1-tert-butyl ester 3-methyl ester as a white solid (2.5 g, 62.5%). MS: 363 (M+H)+

Provenance & Evidence