tert-Butyl hydroperoxide → (R)-4-(8-oxo-5,6,7,8-tetrahydroimidazo[1,5-a]pyridin-5-yl)benzonitrile

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To a round bottom flask was added Rh2(cap)4 (80 mg, 0.09 mmol), NaHCO3 (38 mg, 0.45 mmol) and (R)-4-(5,6,7,8-tetrahydroimidazo[1,5-a]pyridin-5-yl)benzonitrile, CAS #102676-87-9, (200 mg, 0.99 mmol). To this crude was added DCE (10 mL). To this crude was added anhydrous tert-butyl hydroperoxide (1.5 mL, 9.0 mmol). The crude was stirred at 40° C. for overnight. The crude was cooled to room temperature and filtered through celite, and the filtrate was concentrated. The residue was purified via column chromatography using a gradient, CH2Cl2 to 10% (2M NH3 in MeOH)/CH2Cl2 to give 0.12 g of the entitled product. MS 238.0 (M+H), LCMS condition B, retention time 0.50 min. 1H NMR (400 MHz, CDCl3) δ ppm 2.23-2.51 (m, 2H), 2.51-2.65 (m, 2H), 5.40-5.57 (m, 1H), 7.13 (d, 2H), 7.35 (s, 1H), 7.65 (d, 2H), 7.88 (s, 1H).

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