Hydrochloric Acid → 3,3-Difluorocyclopentan-1-amine hydrochloride

Benzyl 3,3-difluorocyclopentylcarbamate (1.5 g, 5.88 mmol) in 6N HCl (6 mL) was heated at 100° C. for 20 h. After the reaction mixture was cooled to rt, the brown solution was extracted with Et2O (2×2 mL) to remove unreacted starting material and toluene. The aqueous phase was dried in the speed vac with heating to give 3,3-difluorocyclopentanamine hydrochloride as a light brown solid (0.79 g, 85% yield). 1H NMR (MeOD-d4, 400 MHz): 4.79 (m, 1H), 2.62 (m, 1H), 2.32 (m, 2H), 2.18 (m, 2H), 1.87 (m, 1H). 13C NMR (MeOD-d4, 400 MHz): 131.4 (t), 41.0 (t), 34.8 (t), 28.9. 19F NMR (MeOD-d4, with CFCl3 as standard, 400 MHz): −93.0 (m, 2F). LC/MS: [M+H]=121.9.

1. extractionthe brown solution was extracted with Et2O (2×2 mL)
2. customto remove unreacted
3. customThe aqueous phase was dried in the speed vac
4. temperaturewith heating

ORD record

ord-2283bf1a033d48f0b3d94c17a1c766ae

Source dataset

uspto-grants-2011_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07888376B2