Acetaldehyde → 2-[N-(Methylmethylene)amino]-4methylpentanoic acid, tert-butyl ester

Reaction equation

[C:1]([O:5][C:6](=[O:13])[C@H:7]([CH2:9][CH:10]([CH3:12])[CH3:11])[NH2:8])([CH3:4])([CH3:3])[CH3:2].[CH:14](=O)[CH3:15].S([O-])([O-])(=O)=O.[Na+].[Na+]>>[CH3:14][CH:15]=[N:8][CH:7]([CH2:9][CH:10]([CH3:11])[CH3:12])[C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:13]

Participants

Reactant 3

HCID 177Acetaldehyde

HCID 24436Sodium Sulfate

HCID 7022311tert-butyl (2S)-2-amino-4-methylpentanoate

Product 1

HCID 589340072-[N-(Methylmethylene)amino]-4methylpentanoic acid, tert-butyl ester

Procedure

A solution of leucine tert-butyl ester (2.0 g, 8.9 mmol) and acetaldehyde (999 ul, 17.9 mmol) was stirred at room temperature for 5 minutes. Anhydrous sodium sulphate was added and the mixture stirred at room temperature for 18 hours. The solid was removed by filtration and the solvent evaporated in vacuo to afford the title compound as an oil.