反应 #1711

反应方程式

lithium aluminum hydride

magnesium sulfate

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

sodium hydroxide

lithium aluminum hydride

→

title compound

收率 72.0%

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

收率 72.0%

溶剂

tetrahydrofuran

ethyl acetate

tetrahydrofuran

反应条件

后处理

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

实验过程

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.

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