Hydrochloric Acid → 2-{[5-(Trifluoromethyl)pyridin-2-yl]methyl}cyclopentan-1-amine hydrochloride
Reaction equation
[F:1][C:2]([F:24])([F:23])[C:3]1[CH:4]=[CH:5][C:6]([CH2:9][CH:10]2[CH2:14][CH2:13][CH2:12][CH:11]2[NH:15]C(=O)OC(C)(C)C)=[N:7][CH:8]=1.[ClH:25]>O1CCOCC1>[ClH:25].[F:23][C:2]([F:1])([F:24])[C:3]1[CH:4]=[CH:5][C:6]([CH2:9][CH:10]2[CH2:14][CH2:13][CH2:12][CH:11]2[NH2:15])=[N:7][CH:8]=1Participants
4
Procedure
To a solution of tert-butyl N-(2-{[5-(trifluoromethyl)pyridin-2-yl]methyl}cyclopentyl)carbamate (1.0 g, 2.9 mmol) in 1,4-dioxane (5 ml) at 0° C. was added drop wise HCl in 1,4-dioxane (12%, 15.0 ml). The reaction was stirred at room temperature for 1 hour, then concentrated in vacuo. To this was then added DCM (50 ml) and a solution of sodium bicarbonate (aq, 7.5%, 15 ml). The organics were dried over sodium sulfate and concentrated in vacuo. The resulting residue was purified by column chromatography (0-2% methanol/DCM) and then treated with HCl in 1,4-dioxane (12%, 5 ml), stirred for 2 hours, concentrated in vacuo, triturated with diethyl ether to afford the title compound as a single diastereomer.