Dimethylamine → HCID 18405246, compound

Participants

Reaction Steps

Methyl 4-(3,4-dichlorobenzyl)-2-formylfuro[3,2-b]pyrrole-5-carboxylate (0.25 g) was dissolved in methanol (5 mL) and THF (10 mL), and to this was added sodium acetate (116 mg) and a portion of MgSO4, followed by dimethylamine solution (2M in methanol, 0.53 mL). After 1 hour, a further 2.5 ml dimethylamine solution was added, followed after 30 min by sodium cyanoborohydride (0.45 g). The reaction was stirred for 18 hours and then quenched by addition of 1M potassium carbonate solution, and extracted with ethyl acetate. Combined organic extracts were dried (MgSO4) and concentrated in vacuo. The residue was purified by column chromatography using ethyl acetate increasing to 10% methanol: ethyl acetate as eluent to give a yellow oil (0.15 g, 55%), NMR d(CDCl3) 2.3 (6H, s), 3.5 (2H, s), 3.8 (3H, s), 5.55 (2H, s), 6.15 (1H, s), 6.85 (1H, s), 6.95 (2H, dd), 7.2 (1H, d), 7.35 (1H, d). M/z (+) 383 (MH+), 381, 338, 336.

Provenance & Evidence