Ammonium Chloride → HCID 118098675, compound

Participants

Reaction Steps

Zinc (1.063 g, 16.25 mmol) was added to a mixture of Intermediate 6B (1 g, 2.95 mmol) and ammonium chloride (3.16 g, 59.1 mmol) in ethanol (10 mL). The mixture was stirred for 3 h at rt and concentrated. Na2CO3 (sat'd, 50 mL) and EtOAc (50 mL) was added and stirred for 1 h. The phases were separated and the aqueous layer was extracted with EtOAc (2×50 mL). The organics were combined, washed with brine, dried over Na2SO4 and concentrated. The crude product was purified by flash chromatography (loading in chloroform, 0% to 50% ethyl acetate in hexane over 30 min using a 40 g silica gel cartridge) to yield Intermediate 6C (600 mg, 1.945 mmol, 65.8% yield) as a yellow oil. 1H NMR (400 MHz, chloroform-d) δ ppm 7.35 (1H, d, J=8.35 Hz), 6.58 (1H, dd, J=8.13, 2.42 Hz), 6.52 (1H, d, J=30.32 Hz), 4.45-4.61 (2H, m), 3.68 (2H, br. s.), 2.75-2.91 (3H, m), 2.03-2.15 (1H, m), 1.41-1.55 (9H, m), 0.83-0.97 (2H, m), 0.64 (2H, q, J=4.54 Hz).

Provenance & Evidence