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

Beteiligte Stoffe

Reaktionsschritte

A 25 mL N,N-dimethylformamide solution of 2.50 g of (4S)-1-(tert-butoxycarbonyl)-4-hydroxy-D-proline and 2.19 g of 1-hydroxybenzotriazole was stirred for 5 minutes under cooling, after which 2.49 g of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride was added, and the reaction mixture was stirred for 30 minutes at the same temperature. After this, 1.95 g of a 50% dimethylamine aqueous solution was added to the reaction solution, and the reaction mixture was stirred for 16 hours at room temperature. Then 100 mL of chloroform and 50 mL of a 5% potassium carbonate aqueous solution were added to the reaction solution, and liquid separation was performed, after which the aqueous layer was extracted with chloroform (30 mL×2), and the combined organic layer was washed with 30 mL of saturated brine and dried with magnesium sulfate, then the drying agent was then filtered off and the solvent was distilled off under reduced pressure. The residue thus obtained was subjected to column chromatography (silica gel 60, mobile phase: ethyl acetate) to obtain 2.74 g of the titled compound (pale yellow solid).

Herkunft & Nachweise