Sodium borohydride → Methyl 4-[5-(2-hydroxyethyl)-1-propylindol-3-ylmethyl]-3-methoxybenzoate
Reaction equation
[BH4-].[Na+].[CH:3]([CH2:5][C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[N:11]([CH2:15][CH2:16][CH3:17])[CH:10]=[C:9]2[CH2:18][C:19]1[CH:28]=[CH:27][C:22]([C:23]([O:25][CH3:26])=[O:24])=[CH:21][C:20]=1[O:29][CH3:30])=[O:4]>CO>[OH:4][CH2:3][CH2:5][C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[N:11]([CH2:15][CH2:16][CH3:17])[CH:10]=[C:9]2[CH2:18][C:19]1[CH:28]=[CH:27][C:22]([C:23]([O:25][CH3:26])=[O:24])=[CH:21][C:20]=1[O:29][CH3:30]Participants
4
Procedure
Sodium borohydride (0.027 g) was added to a stirred solution of methyl 4-[5-(formylmethyl)-1-propylindol-3-ylmethyl]-3-methoxybenzoate (0.54 g) in methanol (15 ml) under a nitrogen atmosphere. After 30 min, the solvent was evaporated. The residue was dissolved in ethyl acetate, washed with water (twice), brine, and then dried (MgSO4) and evaporated. The product was purified by flash chromatography, eluting with 7:3 hexane:ethyl acetate, to give methyl 4-[5-(2-hydroxyethyl)-1-propylindol-3-ylmethyl]-3-methoxybenzoate (0.35 g, 65%) as an oil: partial NMR (300 MHz, DMSO-d6): 0.80(t, 3H, CH3), 1.70(m, 2H, CH2), 2.74(t, 2H, CH2), 3.56(t, 2H, CH2), 3.83(s, 3H, OCH3), 3.91(s, 3H, OCH3), 4.03(m, 4H, NCH2, ArCH2Ar').