[OH:1][CH2:2][CH:3]1[CH2:8][CH2:7][N:6]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:5][CH2:4]1.CCN(CC)CC.[CH3:23][S:24](Cl)(=[O:26])=[O:25].CCOC(C)=O>C1COCC1.O>[CH3:23][S:24]([O:1][CH2:2][CH:3]1[CH2:8][CH2:7][N:6]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:5][CH2:4]1)(=[O:26])=[O:25]
To a mixture of tert-butyl 4-(hydroxymethyl)piperidine-1-carboxylate (Aldrich) (4.30 g, 20 mmol) and Et3N (5 mL) in THF (60 mL) at 0° C. was added MeSO2Cl (1.6 mL) dropwise with stirring. After 2.5 h EtOAc (160 mL) and water (50 mL) were added to the reaction mixture, the EtOAc layer was separated, washed with 1N HCl (30 mL), dried over MgSO4, concentrated in vacuo to obtain the product (5.8 g, 98.9%) as a low melting white solid. This material was used directly for the next step without any further purification. 1H NMR (CDCl3) δ 4.20 (m, 2H), 4.04 (d, 2H, J=6.1 Hz), 2.99 (s, 3H), 2.68 (m, 2H), 2.01-1.70 (m, 3H), 1.43 (s, 9H), 1.20 (m, 2H).
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