To a stirred solution of tetrahydro-4H-pyran-4-one (1 g, 10 mmol) in tetrahydrofuran (THF, 10 mL) was added slowly and dropwise at room temperature methylamine (0.62 g, 20 mmol, 2 M THF solution), followed by acetic acid (0.5 mL). The reaction mixture was stirred continuously for 1 hour. Subsequently, sodium cyanoborohydride (0.7 g, 12 mmol) was added to the reaction mixture at 0 °C and stirring was continued for 16 h at room temperature. The progress of the reaction was monitored by thin layer chromatography (TLC) to confirm the completion of the reaction. Eventually, the target product N-methyltetrahydro-2H-pyran-4-amine (1 g) was isolated as a yellow liquid. Mass spectrum (ESI) m/z 115 [M]+.
