Sodium borohydride → HCID 59326922, compound

Temperature

0 °C

To a solution of methyl 3-(2-fluoropyridin-3-yl)-4-nitrobutanoate (0.991 g, 4.09 mmol) in EtOH (20 mL) at 0° C. was added nickel chloride (0.532 g, 4.10 mmol) and sodium borohydride (1.60 g, 42.3 mmol). The reaction mixture was stirred at 0° C. for 30 min, warmed to room temperature over 30 min, and stirred at room temperature for 30 min. The reaction mixture was quenched with saturated aqueous KH2PO4 and diluted with water and EtOAc. The mixture was filtered through a pad of Celite. The filtrate was extracted with EtOAc (6×) and the combined organic extracts were washed with brine (1×), dried over MgSO4, filtered, and concentrated. Purification by flash column chromatography on silica gel (5% to 10% MeOH in DCM) gave 4-(2-fluoropyridin-3-yl)pyrrolidin-2-one as a colorless oil. MS (ESI, pos. ion) m/z: 181.1 (M+1).

1. temperaturewarmed to room temperature over 30 min
2. stirringstirred at room temperature for 30 min
3. customThe reaction mixture was quenched with saturated aqueous KH2PO4
4. additiondiluted with water and EtOAc
5. filtrationThe mixture was filtered through a pad of Celite
6. extractionThe filtrate was extracted with EtOAc (6×)
7. washthe combined organic extracts were washed with brine (1×)
8. dry with materialdried over MgSO4
9. filtrationfiltered
10. concentrationconcentrated
11. customPurification by flash column chromatography on silica gel (5% to 10% MeOH in DCM)

ORD record

ord-cedcce0a1a3c42a29dccb1cb6f6a6912

Source dataset

uspto-grants-2014_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08637500B2