Aluminium lithium hydride → [3-Amino-5-(1-methyl-1H-tetrazol-5-yl)-phenyl]-methanol
Reaction equation
C([O:3][C:4](=O)[C:5]1[CH:10]=[C:9]([C:11]2[N:15]([CH3:16])[N:14]=[N:13][N:12]=2)[CH:8]=[C:7]([NH2:17])[CH:6]=1)C.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[NH2:17][C:7]1[CH:6]=[C:5]([CH2:4][OH:3])[CH:10]=[C:9]([C:11]2[N:15]([CH3:16])[N:14]=[N:13][N:12]=2)[CH:8]=1Participants
4
Procedure
To a solution of 3-Amino-5-(1-methyl-1H-tetrazol-5-yl)-benzoic acid ethyl ester (250 mg) in THF (5 ml) at 0° C. was added pre-cooled 1M LiAlH4 solution in THF (2 ml) dropwise. This was stirred for 3 h. The reaction mixture was poured onto ice-water and extracted into EtOAc. The organic layer was separated, dried and concentrated in vacuum. Flash chromatography (100:0 to 95:5 gradient DCM:MeOH) afforded the title compound (70 mg).