Allyl bromide → 1-(2-Propenyl)-4-tert-butyloxycarbonyl-2-piperazinone
Reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][NH:11][C:10](=[O:14])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:15](Br)[CH:16]=[CH2:17]>C1COCC1>[CH2:17]([N:11]1[CH2:12][CH2:13][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[CH2:9][C:10]1=[O:14])[CH:16]=[CH2:15]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
4-(tert-Butyloxycarbonyl)-piperazin-2-one (1.0 g, 5.0 mmol), EXAMPLE 40, is alkylated with allyl bromide (0.48 ml, 5.5 mmol) in THF (20 ml) using the procedure described in Example 92, Part A. The title compound (0.92 g, 3.8 mmol) is obtained as a colorless liquid after chromatographed (50% ethyl acetate/hexane). EI MS m/z 240 (M+); 1H NMR (CDCl3, 300 MHz) δ5.80-5.68 (m, 1H), 5.23-5.15 (m, 2H), 4.09 (s, 2H), 4.03 (d, 2H), 3.63 (t, 2H), 3,30 (t, 2H), 1.45 (s, 9H).