Methyl iodide → HCID 70003859, compound

Reaction equation

[CH2:1]([O:8][C:9](=[O:25])[N:10]([CH2:12][C:13](=[O:24])[N:14]([C:16]1[CH:21]=[CH:20][C:19]([CH2:22][OH:23])=[CH:18][CH:17]=1)[CH3:15])[CH3:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[CH3:28]I>CN(C=O)C>[CH2:1]([O:8][C:9](=[O:25])[N:10]([CH2:12][C:13](=[O:24])[N:14]([C:16]1[CH:21]=[CH:20][C:19]([CH2:22][O:23][CH3:28])=[CH:18][CH:17]=1)[CH3:15])[CH3:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Procedure

Under argon to 1.23 g (3.6 mmol) [[(4-Hydroxymethyl-phenyl)-methyl-carbamoyl]-methyl]-methyl-carbamic acid benzyl ester in 40 ml DMF were added 580 mg (13.3 mmol, 3.7 eq, 55% disp) sodium hydride, followed by 3.8 ml (59.6 mmol, 16.6 eq) methyl iodide. The suspension was stirred at RT over night, and added to ice water. The layers were separated and the inorganic one was extracted with 50 ml CH2Cl2 (3×). The combined organic layers were washed with water (2×), dried over MgSO4, filtered and evaporated. Column chromatography on silica gel with a gradient of CH2Cl2/MeOH (100:0-98:2) afforded 0.984 g (77%) [[(4-Methoxymethyl-phenyl)-methyl-carbamoyl]-methyl]-methyl-carbamic acid benzyl ester as a light yellow oil (Rf 0.07 CH2Cl2:MeOH 9:1), MS: 356 (M), +), which was deprotected according to 6.1. to give N-(4-Methoxymethyl-phenyl)-N-methyl-2-methylamino-acetamide as yellow oil (Rf 0.2 CH2Cl2:MeOH 9:1), MS: 223 (MH+).