[CH3:1][O:2][C:3]1[CH:9]=[CH:8][C:6]([NH2:7])=[C:5]([N+:10]([O-:12])=[O:11])[CH:4]=1.[C:13](O)(=O)[CH3:14].[C:17](O[BH-](OC(=O)C)OC(=O)C)(=O)[CH3:18].[Na+].C(=O)(O)[O-].[Na+]>ClCCl>[CH:13]1([CH2:14][NH:7][C:6]2[CH:8]=[CH:9][C:3]([O:2][CH3:1])=[CH:4][C:5]=2[N+:10]([O-:12])=[O:11])[CH2:18][CH2:17]1A 5 L vessel was charged 4-methoxy-2-nitroaniline (160 g, 952 mmol) and dichloromethane (2.44 L), cooled to 10° C. and treated with cyclopropanecarboxyaldehyde (100 g, 143 mmol) in four 25 gram portions. The vessel was charged with acetic acid (300 ml, 523 mmol) via an addition funnel fitted on the reactor and charged to the reaction mixture over 20 minutes. After 45 minutes, the vessel was charged with sodium triacetoxyborohydride (444 g, 209 mmol) portionwise. The mixture was warmed to ambient temperature over 4 hours and was stirred for an additional 14 hours. The mixture was treated with saturated aqueous sodium bicarbonate (100 mL) and poured into sodium bicarbonate (4 L) and dichloromethane. The organic extract was concentrated in vacuo, providing the titled compound.
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