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

HRID 1757410Notes

Reaction equation

HRID 1757410 reaction equation
C1(C[N:8]2[CH2:12][CH2:11][CH:10]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=3)[CH2:9]2)C=CC=CC=1.C([O-])=O.[NH4+]>[Pd].CO.O>[NH:8]1[CH2:12][CH2:11][CH:10]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=2)[CH2:9]1

Participants

6

Reactant 2

HCID 2723923Ammonium formateHCID 109556222-(1-Benzylpyrrolidin-3-yl)pyridine

Product 1

HCID 50139382-(Pyrrolidin-3-yl)pyridineYield 75%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a suspension of 2-[1-(phenylmethyl)-3pyrrolidinyl]pyridine (7.15 g, 30.0mmol) 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 retool) in water (30 mL). The mixture was heated at reflux for 30 minutes, allowed tocool to room temperature, and filtered. The filtrate was concentrated underreduced 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, driedover anhydrous potassium carbonate, and concentrated to a yellow oil. This crude product was chromatographed (silica gel, chloroform-methanol-ammonia75:25:5) to give the title compound (3.33 g, 75%) as a faint yellow liquid.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 30 minutes
  3. customto room temperature
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated underreduced pressure
  6. extractionextracted with dichloromethane (4×15 mL)
  7. concentrationconcentrated to a yellow oil
  8. customThis crude product was chromatographed (silica gel, chloroform-methanol-ammonia75:25:5)

Sources & evidence

ORD record
ord-6aae8b198e094cf18556f7d211453ae1
Source dataset
uspto-grants-1995_08
Patent number
US05446044

Reaction notes

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