1,2,3,4-Tetrahydroisoquinoline → rac-Cyclopent-1-en-1-yl(3,4-dihydroisoquinolin-2(1H)-yl)acetic acid

Participants

Reaction Steps

50 mg (0.45 mmol) of cyclopent-1-en-1-ylboronic acid, 59.5 mg (0.45 mmol) of 1,2,3,4-tetrahydroisoquinoline and 41 mg (0.45 mmol) of glyoxalic acid monohydrate were initially charged in 2 ml of dichloromethane, and 78 μl (57 mg, 0.45 mmol) of N,N-diisopropylethylamine were added. The mixture was stirred at RT for overnight and then concentrated under reduced pressure. The residue was purified by preparative HPLC (RP18 column; acetonitrile/water gradient with addition of 0.1% TFA, 10:90→95:5; run time 38 min) 101 mg (91% purity, 80% of theory) of the title compound were obtained.

Provenance & Evidence