Butylamine → (S)-1-benzyloxycarbonyl-N-butyl-2-pyrrolidinecarboxamide

In 50 ml of THF was dissolved 4.99 g of N-benzyloxycarbonyl-L-proline and then 2.23 g of triethylamine was added to the solution. Then, after slowly adding thereto 2.39 g of ethyl chloroformate under ice-cooling, the reaction was maintained for one hour at 0° C. to 5° C. Then, 2.19 g of n-butylamine was slowly added to the reaction mixture under ice-cooling, the reaction was further performed for one hour at 0° C. to 5° C. The solvent was removed from the reaction mixture, the residue thus formed was dissolved in ethyl acetate, and the solution was washed successively with an aqueous solution of 1N hydrochloric acid, a saturated aqueous sodium hydrogencarbonate solution, and a saturated aqueous sodium chloride solution. The organic layer this formed was collected, dried by Glauber's salt, and then concentrated by dryness. The product was recrystallized from water to provide 4.31 g of (S)-1-benzyloxycarbonyl-N-butyl-2-pyrrolidinecarboxamide (30). M.p. 88°-90° C.

1. additionThen, after slowly adding
2. temperaturethe reaction was maintained for one hour at 0° C. to 5° C
3. temperaturecooling
4. customThe solvent was removed from the reaction mixture
5. customthe residue thus formed
6. washthe solution was washed successively with an aqueous solution of 1N hydrochloric acid
7. customThe organic layer this formed was collected
8. dry with materialdried by Glauber's salt
9. concentrationconcentrated by dryness
10. customThe product was recrystallized from water

ORD record

ord-26facd80d0444cda9e764bbf6f3a0d5c

Source dataset

uspto-grants-1986_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04610821