[O:1]1[CH2:6][CH2:5][CH:4]([CH2:7][NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])[CH2:3][CH2:2]1.I[CH3:17].[H-].[Na+].[NH4+].[Cl-]>CN(C)C=O.C(OCC)(=O)C>[CH3:17][N:8]([CH2:7][CH:4]1[CH2:5][CH2:6][O:1][CH2:2][CH2:3]1)[C:9](=[O:15])[O:10][C:11]([CH3:12])([CH3:14])[CH3:13]
To a solution of tert-butyl N-(4-tetrahydropyranylmethyl)carbamate (610 mg, 2.8 mmol) and iodomethane (805 mg, 5.6 mmol) in 6.0 mL of N,N-dimethylformamide was added sodium hydride (60%, 227 mg, 5.6 mmol) under ice-cooled conditions. After the reaction mixture was stirred at room temperature overnight, the solution was added with saturated NH4Cl aqueous solution, and diluted with ethyl acetate. The separated organic layer was washed with brine, and dried over Na2SO4. After filtration, the filtrate was concentrated in vacuo, and the residue was purified by silica gel column chromatography (hexane/ethyl acetate=90/10 to 70/30) to obtain the title compound (607 mg, 95%).
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