Sodium Bicarbonate → HCID 86762146, compound

Participants

Reaction Steps

To a solution of (4aR,7aR)-7a-(5-bromo-2-fluorophenyl)-4a,5,6,7a-tetrahydro-4H-furo[2,3-d][1,3]thiazin-2-amine (4.8 g, 14.5015 mmol) in 1,4-Dioxane (40 mL) was added di-tert-butyl bicarbonate (6.19 mL, 29.003 mmol) followed by addition of saturated sodium bicarbonate (33.6 mL) and water (4.8 mL) at rt, and the reaction mixture was stirred at rt for 12 h. The reaction mixture was diluted with water (150 mL) and extracted with ethyl acetate (3×100 mL), and the combined organics were dried over the sodium sulphate and concentrated under reduced pressure to give the crude product. The crude product was purified by silica gel column chromatography eluting with 30-40% ethyl acetate-hexanes (combiflash) to give the title compound as a white solid (3.5 g, 56% yield). 1H NMR (400 MHz, CDCl3) δ 7.67 (1H, dd, J=2.4, 6.8 Hz), 7.43 (1H, dt, J=1.2, 6.8 Hz), 6.96 (1H, dd, J=8.4, 11.2 Hz), 4.13 (1H, m), 4.03 (1H, m), 3.26 (1H, m), 2.86 (2H, m), 2.36 (1H, m), 2.21 (1H, m), and 1.47 (9H, s). MS (M+H)+:431.0, 435.0

Provenance & Evidence