Aluminium lithium hydride → 2-(5-amino-1-phenyl-1H-pyrazol-3-yl)-2-methylpropan-1-ol

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+).

1. customThe reaction was carefully quenched by the addition of H2O (0.10 mL), 3M NaOH (0.10 mL) and H2O (0.20 mL)
2. stirringthe mixture was stirred at RT overnight
3. filtrationThe suspension was filtered through Celite
4. washrinsed with EtOAc (20 mL)
5. dry with materialThe filtrate was dried (MgSO4)
6. concentrationconcentrated

ORD record

ord-6c3703bfc48f4f3b8ac53e609f7579b1

Source dataset

uspto-grants-2011_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07897762B2