Dimethylamine → (2S,4R)-tert-butyl 2-(dimethylcarbamoyl)-4-hydroxypyrrolidine-1-carboxylate

Participants

Reaction Steps

To a solution of 25.1 g of (4R)-1-(tert-butoxy carbonyl)-4-hydroxy-L-proline in THF (250 ml) was added 24.9 g of HOBt/H2O and 24.9 g of EDC/HCl under ice cooling, and the reaction mixture was stirred for 15 minutes. To the reaction mixture was added dropwise 10.7 g of an aqueous solution of 50% dimethylamine over 10 minutes, then, the reaction mixture was stirred at room temperature for 15 hours. The solvent was evaporated under reduced pressure, then, an aqueous solution of saturated NaHCO3 was added to the solution, and the resulting mixture was extracted with CHCl3. After drying with Na2SO4, the drying agent was separated by filtration, and the solution was concentrated under reduced pressure. The residue was purified by column chromatography (silicagel 60N; mobile phase: CHCl3/MeOH=20/1 to 9/1; v/v) to obtain 26.2 g of the title compound (colorless solid).

Provenance & Evidence