(3R)-(+)-3-(Dimethylamino)pyrrolidine → Dimethyl-[1-(5-nitro-benzooxazol-2-yl)-pyrrolidin-3-yl]-amine
Reaction equation
CS[C:3]1[O:4][C:5]2[CH:11]=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[CH:8][C:6]=2[N:7]=1.[CH3:15][N:16]([CH3:22])[C@@H:17]1[CH2:21][CH2:20][NH:19][CH2:18]1>C1(C)C=CC=CC=1>[CH3:15][N:16]([CH3:22])[CH:17]1[CH2:21][CH2:20][N:19]([C:3]2[O:4][C:5]3[CH:11]=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[CH:8][C:6]=3[N:7]=2)[CH2:18]1Participants
4
Procedure
Suspend 2-methylsulfanyl-5-nitro-benzooxazole (1.68 g, 7.99 mmol) in toluene (8 mL). Add (3R)-(+)-3-(dimethylamino)pyrrolidine (1.8 mL) and heat to 70° C. overnight. Cool the reaction to room temperature, dilute with toluene (10 mL) and filter. Wash the product with toluene (5 mL) and hexane (10 mL). Dry on the filter flask for 30 min to afford the title compound (1.00 g, 45%). 1H NMR (400 MHz, DMSO-d6): δ 8.03 (d, 1H, J=2.2 Hz), 7.94 (dd, 1H, J=8.6, 2.4 Hz), 7.62 (d, 1H, J=8.8 Hz), 3.81 (dd, 1H, J=10.1, 7.0 Hz), 3.75 (m, 1H), 3.57 (dt, 1H, J=10.0, 7.2 Hz), 3.34 (m, 1H), 2.86 (m, 1H), 2.21-2.13 (m, 7H), 1.87 (m, 1H).