Tetrahydrofuran → Ethyl 4-(3-(naphthalen-2-yl)propanamido)benzoate

Participants

Reaction Steps

Ref. J. of Org. Chem., 2000, 65, 8001. To a stirred solution of amide 42 (0.086 g, 0.249 mmol) and NiCl2 6H2O (0.118 g, 0.498 mmol, 2 eq) in methanol (8 ml) and THF (4 ml) NaBH4 (0.028 g, 0.749 mmol, 4 eq) was added portionwise over 20 min at 0° C. After stirring for 1 h at room temperature, the solvent was distilled off under reduced pressure. Water (10 ml) and ethyl acetate (10 ml) was added. The resulting mixture was filtered through a celite bed which was washed with ethyl acetate (20 ml). After collecting the filtrate, the organic phase was separated, dried over Na2SO4 and the solvent was distilled off under reduced pressure to give the pure product 69 as a white solid (0.066 g, 0.190 mmol, 79%), mp 119-121° C. 1H NMR (400 MHz, CDCl3) δ 1.38 (3H, t, J 7.2 Hz, CH2CH3) 2.75 (2H, t, J 7.2 Hz, CH2CO), 3.23 (2H, t, J 7.2 Hz, CH2—Ar), 4.35 (2H, q, J 7.2 Hz, CH2CH3), 7.12 (1H, bs, N—H), 7.37 (1H, dd, J 1.6, 8.4 Hz, CH, Ar), 7.42-7.50 (4H, m, 4×CH, Ar), 7.69 (1H, bs, CH, Ar), 7.76-7.82 (3H, m, 3×CH, Ar), 7.97 (2H, d, J 9.2 Hz, 2×CH, Ar). MS (API-ES): m/z 348 [M+H]+ (100%), HRMS (API-ES) m/z found 348.1602 [M+H]+.

Provenance & Evidence