Acetic Acid → (1-(4-Hydroxy-4-(6-methoxypyridin-3-yl)cyclohexyl)-3-(methoxymethyl)pyrrolidin-3-yl)(3-(trifluoromethyl)-7,8-dihydro-1,6-naphthyridin-6(5H)-yl)methanone

The title compound was prepared according to general procedures described in Scheme 2: A mixture of 4-hydroxy-4-(6-methoxypyridin-3-yl)cyclohexanone (71 mg, 0.32 mmol), (3-(methoxymethyl)pyrrolidin-3-yl)(3-(trifluoromethyl)-7,8-dihydro-1,6-naphthyridin-6(5H)-yl)methanone VIc (100 mg, 0.29 mmol) and acetic acid (20 μL, 0.34 mmol) in dichloroethane (3 mL) was stirred at room temperature for 0.5 h. Sodium triacetoxyborohydride (123 mg, 0.576 mmol) was added and the reaction mixture was stirred for 2 h at room temperature. After concentration of solvent under reduced pressure, the resulting residue was dissolved in ethyl acetate, then washed with NaHCO3, water and brine. The organic extract was dried, filtered and concentrated. The crude product was obtained as a mixture of isomers which were further separated by reverse phase preparative HPLC to yield isomer A (eluted at 10.092 min) and isomer B (eluted at 11.269 min).

1. stirringthe reaction mixture was stirred for 2 h at room temperature
2. washwashed with NaHCO3, water and brine
3. extractionThe organic extract
4. customwas dried
5. filtrationfiltered
6. concentrationconcentrated

ORD record

ord-6ed87c0d32184f9894cffe87565e1073

Source dataset

uspto-grants-2013_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08569282B2