[OH:1]/[N:2]=[C:3]1\[CH2:4][CH2:5][C:6]2[C:11]\1=[CH:10][C:9]([O:12][CH3:13])=[CH:8][CH:7]=2.CCN(CC)CC.[CH3:21][S:22](Cl)(=[O:24])=[O:23]>CN(C1C=CN=CC=1)C.C(Cl)Cl>[CH3:13][O:12][C:9]1[CH:10]=[C:11]2[C:6]([CH2:5][CH2:4]/[C:3]/2=[N:2]\[O:1][S:22]([CH3:21])(=[O:24])=[O:23])=[CH:7][CH:8]=1
To a solution of (1E)-N-hydroxy-6-methoxy-2,3-dihydro-1H-inden-1-imine (1a, 28.0 g, 158 mmol), DMAP (1.93 g, 15.8 mmol) and Et3N (63.8 g, 632 mmol) in dry DCM (200 mL) was added MsCl (27.5 g, 239 mmol) dropwise at 0° C. After the addition, the resulting solution was stirred at room temperature for 14 hours. The reaction mixture was washed with water (150 mL), saturated NH4Cl (130 mL) and brine (130 mL). The organic layer was dried over Na2SO4 and concentrated under vacuum. The residue was purified by column chromatography (petroleum ether/EtOAc, 1:1) to give (1E)-6-methoxy-N-[(methylsulfonyl)oxy]-2,3-dihydro-1H-inden-1-imine (1b, 27 g, 67%) as a yellow solid.
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