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

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).

1. temperatureunder cooling
2. stirringthe reaction mixture was stirred for 16 hours at room temperature
3. extractionafter which the aqueous layer was extracted with chloroform (30 mL×2)
4. washthe combined organic layer was washed with 30 mL of saturated brine
5. dry with materialdried with magnesium sulfate
6. filtrationthe drying agent was then filtered off
7. distillationthe solvent was distilled off under reduced pressure
8. customThe residue thus obtained

ORD record

ord-b679f796723b47b0a18b1fa350c19401

Source dataset

uspto-grants-2009_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07528124B2