1,2,3,4-Tetrahydro-1-naphthylamine → HCID 67358447, compound

Participants

Reaction Steps

A solution of 1,2,3,4-tetrahydronaphthalen-1-amine (0.030 g, 0.204 mmol), 2-(2-oxo-3,3-diphenylpyrrolidin-1-yl)acetic acid (Example 1C, 0.060 g, 0.204 mmol) and N1-((ethylimino)methylene)-N3,N3-dimethylpropane-1,3-diamine hydrochloride (0.059 g, 0.306 mmol) in dichloromethane (0.5 mL) was stirred at room temperature. After stirring overnight, the reaction was loaded onto a SF15-12 silica gel column (Analogix®, Burlington, Wis.), and the title compound was eluted using a gradient of 5% to 100% ethyl acetate/hexanes over 20 minutes (flow=30 mL/minute). 1H NMR (300 MHz, CDCl3) δ ppm 7.05-7.31 (m, 14H), 5.98-6.03 (m, 1H), 5.05-5.13 (m, 1H), 4.08 (d, J=15.5 Hz, 1H), 4.05 (d, J=15.5 Hz, 1H), 3.51 (t, J=6.5 Hz, 2H), 2.78 (q, J=6.3 Hz, 2H), 2.71 (t, J=6.5 Hz, 2H), 1.85-1.97 (m, 1H), 1.56-1.78 (m, 2H), 1.45-1.55 (m, 1H); MS (ESI−) m/z 423 (M−H)−.

Provenance & Evidence