Borane;tetrahydrofuran → HCID 66704717, compound

Participants

Reaction Steps

To a stirred solution of tert-butyl ethyl(2-(6-nitro-2H-benzo[b][1,4]thiazin-4(3H)-yl)-2-oxoethyl)carbamate (1.01 g, 2.65 mmol) in tetrahydrofuran (5 mL) was added borane-tetrahydrofuran complex (1 M in tetrahydrofuran; 7.94 mL, 7.94 mmol). The resulting mixture was stirred at room temperature for 2 hours. The mixture was then quenched via the slow dropwise addition (to avoid excessive bubbling) of MeOH (5 mL). The quenched reaction was then diluted with ethyl acetate and washed with water (2×) and saturated sodium carbonate (2×). The organic phase was dried, filtered, and concentrated, giving a red-orange oil (925 mg, 95%). 1H NMR (DMSO-d6) δ 7.59-7.41 (m, 1H), 7.39-7.32 (m, 1H), 7.24-7.13 (m, 1H), 3.69-3.62 (m, 2H), 3.58-3.48 (m, 2H), 3.45-3.35 (m, 2H), 3.28-3.16 (m, 2H), 3.15-3.08 (m, 2H), 1.32, 1.24 (2s, 9H), 1.04 (t, J=6.9 Hz, 3H); ESI-MS (m/z, %): 390 (M+Na, 70), 368 (MH+, 12), 312 (47), 268 (100).

Provenance & Evidence