ethyl (2S,5R)-4-allyl-2,5-dimethyl-1-piperazinecarboxylate -Drug Synthesis Database

【结构式】

【分子编号】20689

【品名】ethyl (2S,5R)-4-allyl-2,5-dimethyl-1-piperazinecarboxylate

【CA登记号】

【分子式】C₁₂H₂₂N₂O₂

【分子量】226.31896

【元素组成】C 63.69% H 9.8% N 12.38% O 14.14%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号：(III)

Treatment of trans-2,5-dimethylpiperazine (I) with ethyl chloroformate gave racemic ethyl carbamate (II), which was subsequently alkylated with allyl bromide, and then deprotected with ethanolic KOH to yield racemic piperazine (IV). Separation of the desired enantiomer (V) was achieved through recrystallization of the salt with di-p-toluoyl-D-tartaric acid, followed by liberation of the base with NaOH.

参考文献中间体

合成目标

【1】 Chang, K.-J.; Bishop, M.J.; Bubacz, D.G.; McNutt, R.W. Jr. (Glaxo Wellcome plc); Piperazine cpds. used in therapy. EP 0711289; JP 1997501156; WO 9504051 .
【2】 Chang, K.; Boswell, G.E.; Bubacz, D.G.; Collins, M.A.; Davis, A.O.; McNutt, R.W. (Delta Pharmaceuticals, Inc.); Opioid diarylmethylpiperazines and piperidines. JP 1995503247; US 5658908; US 5681830; WO 9315062 .

中间体序号	中间体编号	品名	分子式	供应商	用于合成
(I)	20687	(2R,5S)-2,5-dimethylpiperazine	C₆H₁₄N₂	详情	详情
(II)	20688	ethyl (2S,5R)-2,5-dimethyl-1-piperazinecarboxylate	C₉H₁₈N₂O₂	详情	详情
(III)	20689	ethyl (2S,5R)-4-allyl-2,5-dimethyl-1-piperazinecarboxylate	C₁₂H₂₂N₂O₂	详情	详情
(IV)	20690	(2R,5S)-1-allyl-2,5-dimethylpiperazine	C₉H₁₈N₂	详情	详情
(V)	20690	(2R,5S)-1-allyl-2,5-dimethylpiperazine	C₉H₁₈N₂	详情	详情

Extended Information