Ammonium formate → 2-(Pyrrolidin-3-yl)pyridine

To a suspension of 2-[1-(phenylmethyl)-3-pyrrolidinyl]pyridine (7.15 g, 30.0 mmol) and 10% palladium on charcoal catalyst (1.90 g) in methanol (120 mL) was added dropwise a solution of ammonium formate (7.57 g, 120 mmol) in water (30 mL). The mixture was heated at reflux for 30 minutes, allowed to cool to room temperature, and filtered. The filtrate was concentrated under reduced pressure, the residue was taken up in water (10 mL), and the solution was made basic with concentrated ammonia and extracted with dichloromethane (4×15 mL). The organic extracts were combined, dried over anhydrous potassium carbonate, and concentrated to a yellow oil. This crude product was chromatographed (silica gel, chloroform-methanol-ammonia 75:25:5) to give the title compound (3.33 g, 75%) as a faint yellow liquid.

1. temperatureThe mixture was heated
2. temperatureat reflux for 30 minutes
3. filtrationfiltered
4. concentrationThe filtrate was concentrated under reduced pressure
5. extractionextracted with dichloromethane (4×15 mL)
6. dry with materialdried over anhydrous potassium carbonate
7. concentrationconcentrated to a yellow oil
8. customThis crude product was chromatographed (silica gel, chloroform-methanol-ammonia 75:25:5)

ORD-Eintrag

ord-045016da71804eba91dc06f55afbd3c6

Quelldatensatz

uspto-grants-1993_06

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US05221676