F[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=1.[CH3:11][CH:12]1[O:17][CH:16]([CH3:18])[CH2:15][NH:14][CH2:13]1.C(NC(C)C)(C)C>O>[CH3:18][C@H:16]1[O:17][C@H:12]([CH3:11])[CH2:13][N:14]([C:2]2[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=2)[CH2:15]1.[CH3:18][C@H:16]1[O:17][C@@H:12]([CH3:11])[CH2:13][N:14]([C:2]2[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=2)[CH2:15]1A mixture of 1-fluoro-4-nitrobenzene, 2,6-dimethylmorpholine (Purchased from Aldrich) and diisopropylamine was heated at 110° C. for 16 h. After being cooled to room temperature, the mixture was added water and extracted with EtOAc. The organic phase was dried over MgSO4, concentrated. The residue was purified by silica gel column chromatograghy eluted with EtOAc:hexanes (5 to 35% EtOAc) to give trans-2,6-dimethyl-4-(4-nitro-phenyl)-morpholine (258 mg) and cis-2,6-dimethyl-4-(4-nitro-phenyl)-morpholine (838 mg) both as yellow solids. Trans-isomer: MS (ES+): m/z=237.2; 1H NMR (CDCl3, 500 MHz): δ 1.30 (d, 6H), 3.17 (dd, 2H), 3.46 (dd, 2H), 4.15-4.22 (m, 2H), 6.77 (d, 2H), 8.14 (d, 2H). Cis-isomer: MS (ES+): m/z=237.2; 1H NMR (CDCl3, 500 MHz): δ 1.29 (d, 6H), 2.62 (dd, 2H), 3.67 (dd, 2H), 3.73-3.81 (m, 2H), 6.84 (d, 2H), 8.14 (d, 2H).
Wird geladen…
