Tetrahydro-4H-pyran-4-one → HCID 178520382, Verbindung

To a solution of N-[(3R)-pyrrolidin-3-yl]-2-[4-(trifluoromethyl)-1H-benzimidazol-2-yl]acetamide (1.0 equiv) in methanol (0.500 M) at room temperature was added tetrahydro-4H-pyran-4-one (1.25 equiv.) followed by sodium triacetoxyborohydride (4 equiv); the reaction mixture was stirred for 16 hours. To the mixture was added NaHCO3 (sat. aq., 10 mL) and dichloromethane (10 mL). The organic layer was separated and the aqueous layer was washed with an addition portion of dichloromethane (10 mL). The organic layers were combined, dried over Na2SO4, filtered and concentrated. The resulting crude product was subjected to flash chromatography (15% MeOH, 1% NH4OH in EtOAc) to afford N-[(3R)-1-(tetrahydro-2H-pyran-4-yl)pyrrolidin-3-yl]-2-[7-(trifluoromethyl)-1H-benzimidazol-2-yl]acetamide as a white solid. 1H-NMR (CD3Cl3) δ: 1.45-1.74 (m, 5H), 2.14-2.22 (m, 2H), 2.33 (m, 1H), 2.60 (m, 2H), 2.83 (m, 1H), 3.34 (m, 2H), 3.91 (m, 2H), 3.95 (s, 2H), 4.39 (m, 1H), 7.27 (t, J=8.0 Hz, 1H), 4.45-7.54 (m, 2H). MS m/z: 397 (M+1).

1. customThe organic layer was separated
2. washthe aqueous layer was washed with an addition portion of dichloromethane (10 mL)
3. dry with materialdried over Na2SO4
4. filtrationfiltered
5. concentrationconcentrated

ORD-Eintrag

ord-5b00fba60672426cab3b300f5b5f95e9

Quelldatensatz

uspto-grants-2011_11

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08067457B2