Reaktion #1711

Reaktionsgleichung

lithium aluminum hydride

magnesium sulfate

(R)-3-(2-methoxyacetylamino)-1-phenylmethylpiperidine

sodium hydroxide

lithium aluminum hydride

→

title compound

Ausbeute 72.0%

(R)-3-(2-methoxyethylamino)-1-phenylmethylpiperidine

Ausbeute 72.0%

Lösungsmittel

tetrahydrofuran

ethyl acetate

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturthe reaction mixture was refluxed for 3 hours
2. 2
   Temperaturthe mixture was refluxed for 3 hours
3. 3
   workup.STIRRINGThe reaction mixture was stirred
4. 4
   Temperaturunder cooling with ice
5. 5
   Filtrationit was filtered with celite
6. 6
   workup.DISTILLATIONThe filtrate was distilled off under reduced pressure
7. 7
   Sonstigethe residue thus obtained
8. 8
   Sonstigewas purified by column chromatography (alumina, ethyl acetate:n-hexane=1:2)

Vorschrift

To a 50 ml anhydrous tetrahydrofuran suspension of 0.87 g (2.0 eg.) of lithium aluminum hydride in a 300 ml round-bottomed flask was added dropwise a 20 ml anhydrous tetrahydrofuran solution of 3.00 g (11.4 mmol) of (R)-3-(2-methoxyacetylamino)-1-phenylmethylpiperidine. After stirred for 1 hour at room temperature, the reaction mixture was refluxed for 3 hours. Further, 0.87 g (2.0 eg.) of lithium aluminum hydride were added and the mixture was refluxed for 3 hours. The reaction mixture was stirred under cooling with ice and, after added 180 ml of ethyl acetate and a 10 ml aqueous solution of sodium hydroxide (1.82 g, 4.0 eg.) in turn to this and stirred for 30 minutes, anhydrous magnesium sulfate was added and it was filtered with celite. The filtrate was distilled off under reduced pressure and the residue thus obtained was purified by column chromatography (alumina, ethyl acetate:n-hexane=1:2) to obtain 2.03 g (yield 72 %) of title compound as a brown oil.

Quelle