[C:1]([CH2:3][C:4]1[C:9]([N+:10]([O-])=O)=[CH:8][C:7]2[C:13]3([CH2:20][O:21][C:6]=2[CH:5]=1)[CH2:18][CH2:17][N:16]([CH3:19])[CH2:15][CH2:14]3)#N.O.C(O)(=O)C>[Pd].C(O)C>[CH3:19][N:16]1[CH2:17][CH2:18][C:13]2([C:7]3[CH2:8][C:9]4[C:4]([CH:3]=[CH:1][N:10]=4)=[CH:5][C:6]=3[O:21][CH2:20]2)[CH2:14][CH2:15]16-(Cyanomethyl)-2,3-dihydro-1'-methyl-5-nitrospiro[benzofuran-3,4'-piperidine] (D6, 0.35 g, 1.2 mmol) was hydrogenated at 50 psiH2 over 10% palladium on charcoal (0.30 g) in a mixture of ethanol (18 ml), water (2 ml) and acetic acid (0.15 ml) for 24 h. Catalyst was filtered off onto kieselguhr, and the filtrate was evaporated to dryness. Chromatography on silica gel, eluting with 0-12% methanol/chloroform (gradient) gave the title compound (0.020 g, 10%) as a pale orange solid.
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