[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[CH:5][C:4]=1[C:12]1[CH:17]=[CH:16][N:15]=[CH:14][CH:13]=1.IC.[BH4-].[Na+].[C:22](=O)([O-])[O-].[K+].[K+]>CC(C)=O.C(O)C.O>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[CH:5][C:4]=1[C:12]1[CH2:13][CH2:14][N:15]([CH3:22])[CH2:16][CH:17]=1A solution of 4-(2-methoxy-5-nitrophenyl)pyridine (D36) (3.4 g, 14.8 mmol) in acetone (150 ml) was treated with excess iodomethane (5 ml) and the mixture stirred at room temperature overnight. The precipitated quaternary salt was filtered off, washed with acetone and dried, giving 5.02 g. This was dissolved in 1:1 ethanol:water (230 ml) and treated portionwise at room temperature, under argon, with sodium borohydride (1.23 g, 32.4 mmol). The mixture was stirred for 1 h at room temperature then potassium carbonate (10 g) was added and the organic layer was separated from the aqueous phase, which was back-extracted with ethyl acetate. The organic phases were combined and dried (Na2SO4) and evaporated under reduced pressure to give the title compound (D37) as an orange oil, which slowly crystallised (3.05 g, 91%).
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