Sodium hydride → (rac)-tert-Butyl 2-(4-(4-(trifluoromethyl)phenyl)-6,7-dihydro-5H-cyclopenta[c]pyridin-7-yloxy)acetate

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Reaction Steps

A cooled (0° C.) solution of (rac)-4-(4-(trifluoromethyl)phenyl)-6,7-dihydro-5H-cyclopenta[c]pyridin-7-ol (example 83) (400 mg, 1.43 mmol) in DMF (4 mL) was treated with NaH (55% in oil, 100 mg, 2.29 mmol) and after ½ h with tert-butyl 2-bromoacetate (201 μL, 1.36 mmol) in DMF (4 mL). After warming up to room temperature overnight, the reaction mixture was poured on aq. 10% KH2PO4 solution followed by extraction with Et2O (3×). The organic phases were washed once with aq. 10% NaCl solution. The combined organic phases were dried (Na2SO4), filtered and purified by flash chromatography (50 g SiO2, Telos-cartridge, 2% 2-propanol in CH2Cl2) to give the title compound (375 mg, 53%) as dark brown oil. MS: 394.2 (M+H+).

Provenance & Evidence