[BH4-].[Na+].[CH2:3]([O:5][C:6](=[O:25])[C:7]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:8][C:9]1[CH:14]=[CH:13][C:12]([NH:15][CH3:16])=[CH:11][C:10]=1[N+:17]([O-:19])=[O:18])[CH3:4].C(O)(=O)C>C(O)C>[CH2:3]([O:5][C:6](=[O:25])[CH:7]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH2:8][C:9]1[CH:14]=[CH:13][C:12]([NH:15][CH3:16])=[CH:11][C:10]=1[N+:17]([O-:19])=[O:18])[CH3:4]Sodium borohydride (NaBH4) (0.2 g, 5.8 mmol) was added to a slurry of the cinnamic ester (2) (3.4 g, 10.5 mmol) in 100 mL of absolute ethanol and the reaction allowed to stir at room temperature for 1.5 hours. Acetic acid (0.5 mL) was added and the mixture concentrated. The residue was dissolved in 250 mL of CHCl3 and was washed with 100 mL of saturated sodium bicarbonate (NaHCO3) solution, and H2O (100 mL). The organic phase was separated, dried (Na2SO4) and concentrated to produce 3.1 g of an orange solid. An analytical sample was obtained by crystallization from methanol(MeOH)-water, m.p. 75°-77° C.
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