Aluminium lithium hydride → 3-(4-Amino-2-(trifluoromethyl)phenyl)-2,2-dimethylpropan-1-ol

Temperature

25 °C

To a mixture of ethyl 3-(4-amino-2-(trifluoromethyl)phenyl)-2,2-dimethylpropanoate (2 g, 6.91 mmol) in THF (200 mL) was added LAH (0.525 g, 13.83 mmol) in portions. The mixture was stirred at 25° C. for 10 h. The mixture was quenched with 15% aqueous NaOH solution (10 mL). The mixture was dried over Na2SO4, filtered, and the filtrate was concentrated. The residue was purified by silica column chromatography (PE/EA=8:1). All fractions found to contain product by TLC (PE/EA=2:1, Rf=0.35) were combined and concentrated to yield a light yellow oil of 3-(4-amino-2-(trifluoromethyl)phenyl)-2,2-dimethylpropan-1-ol (1.1 g, 4.45 mmol, 64% yield): 1H NMR (400 MHz, CD3Cl) δ: 7.17 (d, J=8.4 Hz, 1H), 6.98 (d, J=2.4 Hz, 1H), 6.84 (dd, J=2.4, 8.0 Hz, 1H), 3.31 (s, 2H), 2.67 (d, J=1.2 Hz, 2H), 0.84 (s, 6H); ES-LCMS m/z 248 (M+H).

1. customThe mixture was quenched with 15% aqueous NaOH solution (10 mL)
2. dry with materialThe mixture was dried over Na2SO4
3. filtrationfiltered
4. concentrationthe filtrate was concentrated
5. customThe residue was purified by silica column chromatography (PE/EA=8:1)
6. concentrationconcentrated

ORD record

ord-56094fdbc43242419e13c1b2d4d24892

Source dataset

uspto-grants-2016_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09382238B2