Methanamine, N-methoxy-, hydrochloride (1:1) → Tert-butyl 3-[methoxy(methyl)carbamoyl]pyrrolidine-1-carboxylate

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To a stirred solution of 1-(tert-butoxycarbonyl)pyrrolidine-3-carboxylic acid (4.00 g, 18.6 mmol), N,O-dimethylhydroxylamine hydrochloride (1.69 g, 17.4 mmol), and DIEA (7.5 mL, 41.8 mmol) in CH2Cl2 (80 mL) was added solid EDC.HCl (4.00 g, 20.9 mmol). The mixture was stirred at rt for 18 h and concentrated under reduced pressure. The residue was taken up in ether (175 mL), washed with 5% aq HCl (2×50 mL) and satd aq NaHCO3 (50 mL), and dried over MgSO4. Removal of the solvent left tert-butyl 3-(methoxy(methyl)carbamoyl)pyrrolidine-1-carboxylate (3.16 g, 65%) as an oil.

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