Acetophenone → HCID 11698174, compound

Participants

Reaction Steps

A mixture of 5-aminomethyl-7-methyl-2-(4-trifluoromethoxybenzoyl)-2,3-dihydro-isoindol-1-one (0.053 g, 0.15 mmol), acetophenone (0.036 g, 0.30 mmol), Ti(i-OPr)4 (1 mL), and NaBH3CN (0.1 g, 1.6 mmol) in EtOH (2 mL) was stirred for 6 h. Workup and silica gel column chromatography using 10:1 CHCl3-MeOH afforded 7-methyl-5-[(1-phenyl-ethylamino)-methyl]-2-(4-trifluoromethoxy-benzyl)-2,3-dihydro-isoindol-1-one (0.030 g, 44%). 1H NMR (300 MHz, CDCl3): δ (ppm) 1.38 (d, 3H), 1.64 (bs, 1H), 2.73 (s, 3H), 3.62 (dd, 2H), 3.82 (q, 1H), 4.21 (s, 2H), 4.75 (s, 2H), 7.08-7.39 (m, 11H). GC-MS: m/z 439 (M-15)+.

Provenance & Evidence