Trifluoroacetic acid → 1-((S)-4-(3,4-dichlorophenyl)-3,4-dihydronaphthalen-2-yl)ethanamine

Participants

Reaction Steps

To a solution of tert-butyl-1-((S)-4-(3,4-dichlorophenyl)-3,4-dihydronaphthalen-2-yl)ethylcarbamate 49a (Example 21.3) (100 mg, 0.24 mmol) in CH2Cl2 (2 mL) was added TFA (2 mL). The reaction mixture was stirred for 1 h before being concentrated. The residue was subjected to reverse phase column chromatography (CH3CN/H2O/0.1% formic acid=5% to 100%) to give 46 (66 mg, 86%). 1HNMR (400 MHz, CDCl3) δ 7.34 (d, J=8.4 Hz, 1 H), 7.26 (d, J=2.0 Hz, 1 H), 7.20 (m, 1 H), 7.16-7.08 (m, 2 H), 7.01 (dd, J=1.6, 8.0 Hz, 1H), 6.80 (d, J=7.2 Hz, 1H), 6.46 (s, 1H), 4.09 (t, J=7.6 Hz, 1H), 3.59 (q, J=6.0 Hz, 1 H), 2.60 (dd, J=6.8, 16.4 Hz, 1 H), 2.53 (dd, J=8.4, 16.4 Hz, 1 H), 1.38 (broad, 2 H), 1.14 (d, J=6.8 Hz, 3 H); 13CNMR (100 MHz, CDCl3) δ 144.81, 144.36, 136.15, 134.67, 132.51, 130.52, 130.41, 127.98, 127.77, 127.60, 127.34, 126.70, 120.93, 120.90, 51.91, 43.77, 32.86, 22.11; ESI MS m/z 318.0.

Provenance & Evidence