Methanamine, N-methoxy-, hydrochloride (1:1) → tert-Butyl 4-(methoxy(methyl)carbamoyl)piperidine-1-carboxylate

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Reaction Steps

To a solution of N,O-dimethylhydroxylamine hydrochloride (894 mg, 9.17 mmol), 2-benzotriazol-1-yl-N,N,N′,N′-tetramethyluronio hexafluorphosphate (HBTU) (3.48 g, 9.17 mmol) and diisopropylethylamine (DIPEA) in N,N-dimethylformamide (40 mL) was carefully added 1-(tert-butoxycarbonyl)piperidine-4-carboxylic acid (2 g, 8.73 mmol) and the reaction mixture was stirred at room temperature for 2 days. The mixture was diluted with water (200 mL), extracted with ethyl acetate, washed with aqueous citric acid 5%, aqueous sodium bicarbonate 4%, water, and brine and dried over sodium sulphate. The solvent was removed under reduced pressure and the residue was purified by column chromatography on silica flash, using ethyl acetate as eluent (isocratic), to yield the title compound (2.63 g, 99%) as yellowish oil.

Provenance & Evidence