tert-Butyl (2-(methoxy(methyl)amino)-2-oxoethyl)carbamate → tert-butyl N-(2-oxopropyl)carbamate
Reaction equation
CON(C)[C:4](=[O:14])[CH2:5][NH:6][C:7](=[O:13])[O:8][C:9]([CH3:12])([CH3:11])[CH3:10].[CH3:16][Mg+].[Br-]>C1COCC1>[O:14]=[C:4]([CH3:16])[CH2:5][NH:6][C:7](=[O:13])[O:8][C:9]([CH3:12])([CH3:11])[CH3:10]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of tert-butyl 2-(methoxy(methyl)amino)-2-oxoethylcarbamate (4.36 g, 0.02 mol) in THF (50 mL) added MeMgBr (40 ml, 0.08 ol) at −78° C. The formed mixture was stirred overnight. The mixture was quenched with NH4Cl and extracted with EtOAc. The organic phase was separated, dried over anhydrous Na2SO4, concentrated and purified by column chromatography to give tert-butyl 2-oxopropylcarbamate (2.5 g, 72%). 1H NMR (400 MHz, CDCl3): δ=1.42 (s, 9H), 2.18 (s, 3H), 4.01 (s, 2H), 5.22 (s, 1H).