Hydrochloric Acid → Ethyl 1-aminocyclopentane-1-carboxylate--hydrogen chloride (1/1)

Temperature

23 °C

Cycloleucine ethyl ester ##STR155## A solution of cycloleucine (8.94 g, 69.2 mmol) in EtOH (100 mL) was saturated with HCl gas, and the mixture was stirred at 23° C. for 2 d. The solvents were evaporated in vacuo, the residue was dissolved in water (200 mL) and the solution basified with solid NaHCO3. The aqueous solution was extracted with EtOAc (3×100 mL) and the combined extracts were washed with brine, dried (MgSO4) and evaporated in vacuo. The residue was dissolved in hexane-Et2O (1:1) and a solution of HCl in Et2O-dioxane (0.5 M, 1:1) was added which gave a precipitate. This off-white solid was collected by filtration and dried to give cycloleucine ethyl ester hydrochloride (6.57 g, 33.9 mmol).

1. customThe solvents were evaporated in vacuo
2. dissolutionthe residue was dissolved in water (200 mL)
3. extractionThe aqueous solution was extracted with EtOAc (3×100 mL)
4. washthe combined extracts were washed with brine
5. dry with materialdried (MgSO4)
6. customevaporated in vacuo
7. dissolutionThe residue was dissolved in hexane-Et2O (1:1)
8. additiona solution of HCl in Et2O-dioxane (0.5 M, 1:1) was added which
9. customgave a precipitate
10. filtrationThis off-white solid was collected by filtration
11. customdried

ORD record

ord-b95113d435f446b6a225deecace9b0de

Source dataset

uspto-grants-2000_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06093731