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With hydrogenchloride In ethyl acetate at 20℃; for 1 h;
3,3-Difluorocyclopentanamine hydrochloride The mixture of tert-butyl (3,3-difluorocyclopentyl)carbamate (1 equiv.) in HCl/ethyl acetate (2.00 equiv.) was stirred at room temperature for 1 h. The solid was precipitated. The mixture was filtered and the filter cake was dried in vacuum to afford 3,3-difluorocyclopentanamine hydrochloride (73percent) as a white solid.
Q.B
STEP B: 3,3-difluorocyclopentanamine[0427] A mixture of tert-hvXy 3,3-difluorocyclopentylcarbamate and DCM/TFA (50%, 7 mL) was stirred at 25°C for 30 min. The reaction mixture was concentrated down and dried in vacuo to afford the title compound as an orange semi-solid, TFA salt (0.51 g, 99%). 1H NMR (400 MHz, DMSO-J6) δ 1.69 - 1.88 (m, 1 H) 2.00 - 2.22 (m, 3 H) 2.22 - 2.38 (m, 1 H) 2.56 (d, J=6.32 Hz, 1 H) 3.71 (d, J=5.31 Hz, 1 H) 8.20 (br. s., 3 H).
With (bis-(2-methoxyethyl)amino)sulfur trufluoride; In dichloromethane; at 0 - 20℃; for 18h;
PREPARATION Q: 3,3-difluorocyclopentanamine[0424] STEP A: tert-butyi S^-difluorocyclopentylcarbamate[0425] Deoxofluor (0.658 mL, 5.02 mmol) was added dropwise to a solution otert- butyl 3-oxocyclopentylcarbamate (0.5 g, 2.509 mmol) in DCM (12 mL) at 00C. After complete addition, the reaction mixture was allowed to warm up to room temperature and was stirred for 18 h. The reaction mixture was poured slowly into ice-cold aqueous NaHCO3 (sat.). The aqueous layer was extracted 3 times with DCM. The combined organic layers were dried over MgSO4, concentrated, and dried in vacuo. Purification by silica column chromatography (MeOH/DCM, 0-5%) afforded the title compound as a yellow oil (0.52 g, 94%).
36%
With diethylamino-sulfur trifluoride; In dichloromethane; at 20℃; for 20h;Inert atmosphere;
tert-Butyl(3,3-difluorocyclopentyl)carbamate To a mixture of <strong>[847416-99-3]tert-butyl (3-oxocyclopentyl)carbamate</strong> (1 equiv.) in DCM (0.2 M) was added DAST (5.00 equiv.) in one portion at room temperature under N2. The mixture was stirred at room temperature for 20 h. The mixture was poured into ice-water (w/w=1/1) and stirred for 20 min. The aqueous phase was extracted with DCM. The combined organic phase was washed with saturated brine, dried over anhydrous Na2SO4, filtered and concentrated in vacuum to give a residue. The residue was purified by silica gel chromatography to afford tert-butyl (3,3-difluorocyclopentyl)carbamate (36%) as a white solid. 1H NMR (400 MHz, CDCl3) delta ppm: 4.68 (s, 1H), 4.19-4.17 (m, 1H), 2.54 (qd, J=14.28, 7.97 Hz, 1H), 2.23-2.21 (m, 2H), 2.21-2.09 (m, 2H), 1.70-1.68 (m, 1H), 1.46 (s, 9H).
With hydrogenchloride In ethyl acetate at 20℃; for 1h;
40 3,3-Difluorocyclopentanamine hydrochloride
3,3-Difluorocyclopentanamine hydrochloride The mixture of tert-butyl (3,3-difluorocyclopentyl)carbamate (1 equiv.) in HCl/ethyl acetate (2.00 equiv.) was stirred at room temperature for 1 h. The solid was precipitated. The mixture was filtered and the filter cake was dried in vacuum to afford 3,3-difluorocyclopentanamine hydrochloride (73%) as a white solid.
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