Water → HCID 19784181, compound

Participants

Reaction Steps

Lithium diisopropylamide (3.7 ml of a 1.5M solution in THF, 5.58 mmol) was added dropwise to a solution of 3-carbomethoxy-5,5-dimethoxy-1-azabicyclo[2.2.1]heptane (1 g, 4.7 mmol) in THF (40 ml), at -78° C., and stirred for 2 h. A solution of 2-iodopyrazine (1.15 g, 5.58 mmol) in THF (5 ml) was added, at -78° C., stirred for 1 h, and then warmed to room temperature and stirred for 16 h. Water (25 ml) and dichloromethane (70 ml) were added and the aqueous extracted with dichloromethane (3×100 ml). The combined extracts were dried (Na2SO4), evaporated, and the crude product chromatographed through silica-gel using dichloromethane/methanol (92:8) as eluant to give the title compound as a yellow liquid (0.1 g); (Found: M+ =293.1378; C14H19N3O4 requires M+ =293.1376); m/e 293 (M+); δ (360 MHz, CDCl3) 2.34 (1H, d, J=16 Hz, CH of CH2N); 2.82 (1H, s, CH-bridgehead); 3.05 (1H, dd, J=4.3 and 14.6 Hz, CH of CH2 --N); 3.18 (3H, s, OMe); 3.20 (1H, dd, J=3.3 and 8.5 Hz, CH of CH2 --N); 3.28 (1H, d, J=12.7 Hz, CH of CH2 --N); 3.34 (3H, s, OMe); 3.59 (3H, s, CO2Me); 3.67 (1H, d, J=10.8 Hz, CH of CH2 --N); 3.91 (1H, dd, J=3 and 12.7 Hz, CH of CH2 --N); 8.45 (1H, d, J=3.7 Hz, pyrazine-H); 8.51 (1H, dd, J=2.5 and 3.7 Hz, pyrazine-H); 8.58 (1H, d, J=2.5 Hz, pyrazine-H).

Provenance & Evidence