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Intermediate 36: 2-[5-(Trifluoromethyl)pyridin-2-yl]methyl}cyclopentan-1-amine hydrochloride Step (i): [5-(Trifluoromethyl)pyridin-2-yl]methanol To the solution of 2-iodo-5-(trifluoromethyl)pyridine (CAS number 100366-75-4; 10 g, 69.4 mmol) in toluene (250 ml) at -78 C. was added n-BuLi in hexane (2.5 M, 15.0 mL, 37.5 mmol). The reaction was stirred at -78 C. for 15 minutes. To this was then added drop wise DMF (3.5 ml) and then stirred at -78 C. for 1 hour. Sodium borohydride (2.74 g, 72.0 mmol) and methanol (50 ml) were added and the resulting reaction mixture was stirred for 30 minutes and then allowed to warm to room temperature. The reaction was cooled to -10 C. and to this was then added a saturated solution of ammonium chloride. The organics were extracted with ethyl acetate (2×200 ml) and the combined organics were washed with brine, dried over sodium sulfate and concentrated in vacuo to afford the title compound which was used without further purification. 1H NMR (400 MHz, DMSO) delta ppm 4.66-4.65 (m, 2H), 5.69-5.66 (m, 1H), 7.71-7.69 (m, 1H), 8.23-8.21 (m, 1H), 8.87 (s, 1H) MS ES+: 178
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