Acetone → HCID 57949816, compound

Participants

Reaction Steps

A mixture of 5-aminomethyl-2-(4-trifluoromethoxy-benzyl)-7-trifluoromethyl-2,3-dihydro-isoindol-1-one (0.040 g, 0.1 mmol), paraformaldehyde (0.025 g), acetone (0.5 mL), NaCNBH3 (0.013 g, 0.2 mmol), and anhydrous MgSO4 (0.050 g) in MeOH (6 mL) was stirred for 6 h. Workup and silica gel column chromatography using 10:1 CHCl3-MeOH afforded 5-[(isopropyl-methyl-amino)-methyl]-2-(4-trifluoromethoxy-benzyl)-7-trifluoromethyl-2,3-dihydro-isoindol-1-one (0.017 g, 39%). 1H NMR (300 MHz, CDCl3): δ ppm) 1.02 (d, 6H), 2.12 (s, 3H), 2.88 (q, 1H), 3.61 (s, 2H) 4.24 (s, 2H), 4.78 (s, 2H), 7.18 (d, 2H), 7.37 (d, 2H), 7.58 (s, 1H), 7.71 (s, 1H). GC-MS: m/z 445 (4-15)+, 367 (M−93)+.

Provenance & Evidence