Borane;tetrahydrofuran → HCID 59144132, compound

Participants

Reaction Steps

A solution of tert-butyl ethyl(2-(7-nitro-2H-benzo[b][1,4]thiazin-4(3H)-yl)-2-oxoethyl)carbamate (0.8 g, 2.097 mmol) in anhydrous tetrahydrofuran (5 mL) was treated with borane-THF complex (1M in THF; 6.29 mL, 6.29 mmol) and stirred at room temperature for 3 hours. The reaction was quenched dropwise with methanol (10 mL) and then concentrated. The crude residue was diluted with methanol (25 mL) and refluxed for 10 minutes. The mixture was then concentrated, and the residue was subjected to column chromatography on silica gel (1:9-3:7 EtOAc:CH2Cl2) to give a yellow syrup (0.493 g, 64%). 1H-NMR (DMSO-d6) δ 7.85-7.78 (m, 2H), 6.94-6.85 (m, 1H), 3.76-3.79 (m, 2H), 3.62-3.57 (m, 2H), 3.37-3.33 (m, 2H), 3.22-3.19 (m, 2H), 3.08-3.04 (m, 2H), 1.35 and 1.30 (2×brs, 9H), 1.03 (t, J=6.9 Hz, 3H). ESI-MS (m/z, %): 390 (M+Na, 67%), 368 (MH+, 17%), 312 (83%), 268 (100%).

Provenance & Evidence