Hydrochloric Acid → HCID 24904904, compound

To a stirred solution of tert-butyl [(3R)-1-(4-methylbenzyl)-3-pyrrolidinyl]carbamate (4.6 g) in ethyl acetate (10 mL) was added 4N hydrogen chloride in ethyl acetate (60 mL) at ambient temperature and the resulting mixture was stirred at the same temperature for three hours. The mixture was concentrated in vacuo and the residual syrup was dissolved in chloroform (100 mL). To this solution was added saturated sodium bicarbonate (50 mL) and the resulting biphasic mixture was vigorously stirred at ambient temperature for half an hour. The organic layer was separated and the aqueous layer was reextracted with chloroform (50 mL) two times. The combined organic layer was dried over anhydrous sodium sulfate and evaporated in vacuo to afford (3R)-1-(4-methylbenzyl)-3-pyrrolidinamine (2.1 g) as a pale brown viscous oil, which was used in the next step without further purification.

1. concentrationThe mixture was concentrated in vacuo
2. dissolutionthe residual syrup was dissolved in chloroform (100 mL)
3. additionTo this solution was added saturated sodium bicarbonate (50 mL)
4. stirringthe resulting biphasic mixture was vigorously stirred at ambient temperature for half an hour
5. customThe organic layer was separated
6. dry with materialThe combined organic layer was dried over anhydrous sodium sulfate
7. customevaporated in vacuo

ORD record

ord-6cc96aecadbc4f98ad8a6c0f015ef709

Source dataset

uspto-grants-2008_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07465731B2