Dimethylamine → phenylmethyl (2S)-2-[(dimethylamino)carbonyl]-1-piperidinecarboxylate

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Reaction Steps

(2S)-1-{[(Phenylmethyl)oxy]carbonyl}-2-piperidinecarboxylic acid (2.0 g, 7.595 mmol) and HOBt (1.231 g, 9.114 mmol) were dissolved in CH2Cl2 (40 mL), and 4-methylmorpholine (2.5 mL, 22.78 mmol), 2.0 M solution of dimethyl amine in THF (4.55 mL, 9.114 mmol), and EDCI (1.750 g, 9.114 mmol) were added. This solution was stirred overnight, and was then washed with 1 N HCl (25 mL) and the aqueous layer was extracted with CH2Cl2 (3×25 mL). The combined organic layers were dried over anhydrous MgSO4 and concentrated in vacuo. This crude product was purified by flash chromatography (Combiflash, 0-100% ethyl acetate/hexanes) to provide phenylmethyl (2S)-2-[(dimethylamino)carbonyl]-1-piperidinecarboxylate (1.919 g, 87%). LCMS: (M+H)+: 291.1.

Provenance & Evidence