N1CCCC1.[OH:6][C:7]1[CH:12]=[C:11]([O:13][CH3:14])[C:10]([N+:15]([O-:17])=[O:16])=[CH:9][C:8]=1[C:18](=O)[CH3:19].[CH3:21][N:22]1[CH2:27][CH2:26][C:25](=O)[CH2:24][CH2:23]1>CO>[CH3:14][O:13][C:11]1[CH:12]=[C:7]2[C:8]([CH:18]=[CH:19][C:25]3([O:6]2)[CH2:26][CH2:27][N:22]([CH3:21])[CH2:23][CH2:24]3)=[CH:9][C:10]=1[N+:15]([O-:17])=[O:16]Pyrrolidine (1.15 mL, 13.8 mmol) was added to 1-(2-Hydroxy-4-methoxy-5-nitro-phenyl)-ethanone (2.57 g, 12.2 mmol) (Banks, C. K.; Hamilton, C. S. J. Am. Chem. Soc. 1938, 60, 1370) and 1-Methyl-piperidin-4-one (1.60 mL, 13.0 mmol) in Methanol (50.0 mL) and the reaction was stirred under an atmosphere of nitrogen. After overnight stirring, ˜50% conversion was achieved. The mixture was heated at 50° C. for 30 h. Following basic workup, the crude material was purified on ISCO (0-12% MeOH:DCM) to afford 7-methoxy-1′-methyl-6-nitrospiro[chromene-2,4′-piperidin]-4-((3H)-one (2.42 g; Yield=64.9%).
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