Aluminium lithium hydride → 2-(5-amino-1-phenyl-1H-pyrazol-3-yl)-2-methylpropan-1-ol
Reaction equation
[NH2:1][C:2]1[N:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[N:5]=[C:4]([C:13]([CH3:20])([CH3:19])[C:14](OCC)=[O:15])[CH:3]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[NH2:1][C:2]1[N:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[N:5]=[C:4]([C:13]([CH3:20])([CH3:19])[CH2:14][OH:15])[CH:3]=1Participants
4
Procedure
To a stirring solution of ethyl 2-(5-amino-1-phenyl-1H-pyrazol-3-yl)-2-methylpropanoate (DP-2440, 0.240 g, 0.86 mmol) in dry THF (8.0 mL) at RT was added LiAlH4 (1.0 M in THF, 2.6 mL, 2.6 mmol) and the resulting mixture was stirred at RT for 1 h. The reaction was carefully quenched by the addition of H2O (0.10 mL), 3M NaOH (0.10 mL) and H2O (0.20 mL), and the mixture was stirred at RT overnight. The suspension was filtered through Celite and rinsed with EtOAc (20 mL). The filtrate was dried (MgSO4) and concentrated to afford 2-(5-amino-1-phenyl-1H-pyrazol-3-yl)-2-methylpropan-1-ol (0.208, 105% yield) as a yellow oil. MS (ESI) m/z: 232.2 (M+H+).