반응 #1711

반응 방정식

lithium aluminum hydride

magnesium sulfate

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

sodium hydroxide

lithium aluminum hydride

→

title compound

수율 72.0%

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

수율 72.0%

용매

tetrahydrofuran

ethyl acetate

tetrahydrofuran

반응 조건

후처리

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

실험 절차

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.

출처