Hydrochloric Acid → 3,3-Difluorocyclopentan-1-amine hydrochloride
Reaction equation
[F:1][C:2]1([F:18])[CH2:6][CH2:5][CH:4]([NH:7]C(=O)OCC2C=CC=CC=2)[CH2:3]1.[ClH:19]>>[ClH:19].[F:1][C:2]1([F:18])[CH2:6][CH2:5][CH:4]([NH2:7])[CH2:3]1Participants
3
Procedure
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.
Workup
- extractionthe brown solution was extracted with Et2O (2×2 mL)