Methyl vinyl ketone → 3-{[(2,4-Dichlorobenzyl)-(3-oxo-butyl)-amino]-methyl}-azetidine-1-carboxylic acid tert-butyl ester
Reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:11][CH:10]([CH2:12][NH:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:16]=2[Cl:22])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH:23]([C:25]([CH3:27])=[O:26])=[CH2:24]>C(Cl)(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[CH2:11][CH:10]([CH2:12][N:13]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:16]=2[Cl:22])[CH2:24][CH2:23][C:25](=[O:26])[CH3:27])[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 3-[(2,4-dichlorobenzylamino)-methyl]-azetidine-1-carboxylic acid tert-butyl ester (200 mg, 0.58 mmol) in CHCl3 (3 mL) is added methyl vinyl ketone (0.12 mL, 1.45 mmol). The reaction is refluxed under N2 overnight and concentrated. The crude product is purified by flash chromatography on silica gel eluting with 5% EtOH (10% NH4OH)/chloroform to yield 196 mg (81%) of 3-{[(2,4-dichlorobenzyl)-(3-oxo-butyl)-amino]-methyl}-azetidine-1-carboxylic acid tert-butyl ester. 1H NMR (400 MHz, CD3OD) δH: 7.46-7.44 (2H, m), 7.35-7.32 (1H, m), 3.95-3.91 (2H, m), 3.7 (2H, s) 3.5-3.45 (2H, m), 2.9-2.75 (3H, m), 2.74-2.65 (4H, m), 2.1 (3H, s), 1.46 (9H, s). Mass spectrum (ion spray): m/z=415.2 (M+H).