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

HRID 2036028

Reaktionsgleichung

[C:1]([O-:4])(O)=O.[Na+].[CH:6]1[N:7]=[CH:8][N:9]2[C@@H:14]([C:15]3[CH:22]=[CH:21][C:18]([C:19]#[N:20])=[CH:17][CH:16]=3)[CH2:13][CH2:12]C[C:10]=12.C(OO)(C)(C)C>C1CCNC(=O)CC1.C1CCNC(=O)CC1.C1CCNC(=O)CC1.C1CCNC(=O)CC1.[Rh].[Rh].ClCCCl>[O:4]=[C:1]1[CH2:12][CH2:13][C@H:14]([C:15]2[CH:22]=[CH:21][C:18]([C:19]#[N:20])=[CH:17][CH:16]=2)[N:9]2[CH:8]=[N:7][CH:6]=[C:10]12

Komponenten

Reaktionsbedingungen

Temperatur: 40 °C

Versuchsvorschrift

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).

Aufarbeitung

temperatureThe crude was cooled to room temperature
filtrationfiltered through celite
concentrationthe filtrate was concentrated
customThe residue was purified via column chromatography

Quellen und Nachweise

ORD-Eintrag: ord-c10da908997649bda44dd7ed1b54f5bd
Quelldatensatz: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08575160B2

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