Sodium Hydroxide → 8-Cyclohexyl-3h-dipyrrolo[1,2-a:2',3'-e]pyrazine

Temperature

90 °C

To a solution of 8-cyclohexyl-3-tosyl-3H-dipyrrolo[1,2-a:2′,3′-e]pyrazine (0.015 g, 0.038 mmol) in 1,4-dioxane (3 mL) was added aqueous NaOH (2 N, 0.29 mL, 0.57 mmol). The reaction mixture was heated to about 90° C. After about 15 h, the reaction mixture was cooled to ambient temperature and diluted with EtOAc (5 mL) and saturated aqueous NH4Cl (5 mL). The organic layer was separated, washed with water (5 mL) followed by brine (5 mL), dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure. The residue was triturated with EtOAc/heptane (1:1, 1 mL). The resulting solid was collected by filtration and dried in vacuo to provide 8-cyclohexyl-3H-dipyrrolo[1,2-a:2′,3′-e]pyrazine as a tan solid (0.005 g, 55%). LC/MS (Table 2, Method a) Rt=2.78 min; MS m/z: 240 (M+H)+.

1. temperaturethe reaction mixture was cooled to ambient temperature
2. customThe organic layer was separated
3. washwashed with water (5 mL)
4. dry with materialdried over anhydrous Na2SO4
5. filtrationfiltered
6. concentrationconcentrated under reduced pressure
7. customThe residue was triturated with EtOAc/heptane (1:1, 1 mL)
8. filtrationThe resulting solid was collected by filtration
9. customdried in vacuo

ORD record

ord-6a281957b33d45b488dd176c0e701b7b

Source dataset

uspto-grants-2016_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09365579B2