HCID 131725691, Verbindung → 1-(2-Methoxyethyl)piperidine-4-carbaldehyde

Temperatur

-78 °C

1-(2-Methoxyethyl)-piperidine-4-carboxylic acid ethyl ester A solution of ethyl isonipecotate (26 g, 166 mmol) in ethanol (150 ml) was treated with potassium carbonate (41 g, 297 mmol) and 2-bromoethyl methyl ether (25 g, 179 mmol). The reaction mixture was heated to reflex for 24 hours, cooled and then filtered. The filtrate was concentrated in vacuo to yield the title compound (32.76 g, 92%); MS(ES+) m/e 216 [M+H]+. Step 2. 1-(2-Methoxyethyl)-piperidine-4-carbaldehyde Diisobutylaluminium hydride (10.2 ml, 1M solution in THF) was added to a solution of the product of Step 1 (2.0 g, 9.3 mmol) in toluene (40 ml) over a period of 1 hour at −78° C. The reaction was stirred at −78° C. for 1 hour and then quenched with methanol (5 ml) and aqueous ammonium acetate solution (5 ml). The mixture was stirred for 1 hour and then filtered through celite. The filtrate was concentrated in vacuo to yield the title compound (1.1 g, 69%); MS(ES+) m/e 172 [M+H]+.

1. customquenched with methanol (5 ml) and aqueous ammonium acetate solution (5 ml)
2. stirringThe mixture was stirred for 1 hour
3. filtrationfiltered through celite
4. concentrationThe filtrate was concentrated in vacuo

ORD-Eintrag

ord-6b97a1e8a1924347bfb4e3c9012319de

Quelldatensatz

uspto-grants-2006_04

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07026336B1