Ethyl 3-pyridylacetate → Ethyl 2-(piperidin-3-yl)acetate

Commercially available ethyl-3-pyridylacetate (4.04 g; 24.5 mmol) was dissolved in absolute ethanol (100 ml). L(+) tartaric acid (3.67 g; 24.5 mmol) and platinum oxide (546.1 mg; 2.4 mmol) were added, and the partial suspension was placed under hydrogen gas at 50 psi with shaking for 24 hours. The hydrogen was removed, and the mixture was then filtered through celite to remove the catalyst. The filtrate was evaporated at ambient temperature under reduced pressure to a small volume. This residue was diluted with saturated sodium bicarbonate solution and extracted with ethyl acetate. The aqueous solution was then basified with 1 N sodium hydroxide and extracted with fresh ethyl acetate. The ethyl acetate extracts were combined, dried with anhydrous potassium carbonate, and evaporated at ambient temperature under reduced pressure, giving ethyl 3-piperidinylacetate (2.96 g) as a very pale yellow oil without further purification. MS m/z (positive ion) 172 (MH+; 100).

1. customThe hydrogen was removed
2. filtrationthe mixture was then filtered through celite
3. customto remove the catalyst
4. customThe filtrate was evaporated at ambient temperature under reduced pressure to a small volume
5. additionThis residue was diluted with saturated sodium bicarbonate solution
6. extractionextracted with ethyl acetate
7. extractionextracted with fresh ethyl acetate
8. dry with materialdried with anhydrous potassium carbonate
9. customevaporated at ambient temperature under reduced pressure

ORD-Eintrag

ord-14d9baefebac4a1dacf7976f9fd2c3de

Quelldatensatz

uspto-grants-2003_12

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US06664271B1