Isopropylamine → HCID 68770231, compound

Participants

Reaction Steps

HATU (0.159 g, 0.42 mmol) was added to a solution of (+)-(trans)-2-{4-[(3-phenoxybenzyl)amino]phenyl}cyclopropanecarboxylic acid (III-3b) (0.100 g, 0.28 mmol) in 3 ml of N,N-dimethylformamide. The mixture was stirred at room temperature for 10 minutes and 0.059 mL (0.69 mmol) of isopropylamine was added. After stirring at room temperature for 15 minutes, the reaction mixture was diluted with water and extracted with ethyl acetate. The organic phase was washed with water and brine, dried over anhydrous sodium sulfate and concentrated. Chromatography on silica gel with hexane:ethyl acetate gave 0.068 g (61% yield) of the title compound as a white powder. NMR (400 MHz, CDCl3) δ 7.32 (d, J=8.61 Hz, 2H), 7.28 (d, J=8.6 Hz, 2H), 7.10 (t, J=8.42 Hz, 1H), 7.00 (m, 1H), 6.97 (d, J=6.59 Hz, 2H), 6.89 (d, J=8.61 Hz, 2H), 6.87 (m, 1H), 6.52 (d, J=8.61 Hz, 2H), 5.37 (d, J=7.51 Hz, 1H), 4.27 (s, 2H), 4.10 (septet, J=6.59 Hz, 1H), 4.00 (br s, 1H), 2.36 (m, 1H), 1.52 (m, 1H), 1.40 (m, 1H), 1.15 (d, J=4.21 Hz, 3H), 1.14 (d, J=4.40 Hz, 3H), 1.10 (m, 1H). ES-MS m/z 401 (M-H)+. [α]25,D=+183° (chloroform, c=1.5).

Provenance & Evidence