Trifluoroacetic acid → (2S)-1-[4-chloro-2-(1,1,1-trifluoro-2-methylpropan-2-yl)phenoxy]propan-2-amine

Trifluoroacetic acid (5 mL) was added to a solution of tert-butyl {(2S)-1-[4-chloro-2-(1,1,1-trifluoro-2-methylpropan-2-yl)phenoxy]propan-2-yl}carbamate (C49) (600 mg, 1.52 mmol) in dichloromethane (24 mL), and the reaction mixture was stirred for 30 minutes. Aqueous sodium hydroxide solution (1 M, 50 mL) was added, and the mixture was extracted with diethyl ether (3×50 mL). The combined organic layers were dried over magnesium sulfate, filtered, and concentrated in vacuo to afford the product as a light amber oil, which was used without further purification. Yield: 433 mg, 1.46 mmol, 96%. LCMS m/z 296.1, 298.1 (M+1). 1H NMR (400 MHz, CDCl3) δ 1.24 (d, J=6.4 Hz, 3H), 1.67 (br s, 6H), 2.13 (br s, 2H), 3.41-3.50 (m, 1H), 3.79 (dd, half of ABX pattern, J=8.8, 7.2 Hz, 1H), 3.86 (dd, half of ABX pattern, J=8.9, 4.4 Hz, 1H), 6.86 (d, J=8.8 Hz, 1H), 7.23 (dd, J=8.8, 2.5 Hz, 1H), 7.36-7.39 (m, 1H).

1. extractionthe mixture was extracted with diethyl ether (3×50 mL)
2. dry with materialThe combined organic layers were dried over magnesium sulfate
3. filtrationfiltered
4. concentrationconcentrated in vacuo

ORD record

ord-a37adcd4351b4696a5ebf390bd317e7f

Source dataset

uspto-grants-2015_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09067934B2