Magnesium → tert-butyl 2,3,4,5-tetrahydro-1H-benzo[b]azepin-4-ylcarbamate

Participants

Reaction Steps

To a solution of tert-butyl 1-tosyl-2,3,4,5-tetrahydro-1H-benzo[b]azepin-4-ylcarbamate (0.6 g, 1.4 mmol) in methanol (33 mL) was added magnesium metal turnings (0.51 g, 0.021 mol). The reaction mixture was stirred for 4 hours at room temperature before being evaporated to dryness and diluted with dichloromethane. The suspension formed was filtered through celite and the filtrate washed with brine. The organic layer was dried over anhydrous sodium sulfate concentrated under vacuo to give a residue which was purified by silica gel column chromatography eluting with (0-10% ethyl acetate in hexanes) to afford tert-butyl 2,3,4,5-tetrahydro-1H-benzo[b]azepin-4-ylcarbamate (0.3 g). 1H NMR: (400 MHz, CDCl3) δ: 7.18-7.08 (m, 2H), 6.92 (t, 1H), 6.84 (d, 1H), 4.52 (bs, 1H), 3.92 (m, 1H), 3.78 (bs, 1H), 3.14-2.98 (m, 2H), 3.88-3.78 (m, 1H), 2.06-2.0 (m, 1H), 1.96-1.88 (m, 1H), 1.6 (bs, 1H), 1.42 (s, 9H).

Provenance & Evidence