1-(3-bromo-1,1-dimethylpropyl)benzene -Drug Synthesis Database

【结构式】

【分子编号】38639

【品名】1-(3-bromo-1,1-dimethylpropyl)benzene

【CA登记号】

【分子式】C₁₁H₁₅Br

【分子量】227.1441

【元素组成】C 58.17% H 6.66% Br 35.18%

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：(VI)

The cyclization of pyridine-3-carbaldehyde (I) with L-cysteine (II) gives 2-(3-pyridyl)thiazolidine-4(R)-carboxylic acid (III), which is finally condensed with 1-(3-methyl-3-phenylbutyl)piperazine (IV) by means of DCC and HOBT In DMF. The intermediate 1-(3-methyl-3-phenylbutyl)piperazine (IV) has been obtained as follows: The reduction of 3-methyl-3-phenylbutyric acid (IV) with LiAlH4 in THF gives the corresponding butanol (V), which is treated with refluxing 48% HBr to yield the 3-methyl-3-phenylbutyl bromide (VI). The condensation of (VI) with piperazine-1-carboxylic acid ethyl ester (VII) by means of K2CO3 in 2-butanone gives 4-(3-methyl-3-phenylbutyl)piperazine-1-carboxylic acid ethyl ester (VIII), which is decarboxylated with NaOH in refluxing ethanol.

参考文献中间体

合成目标

【1】 Mase, T.; Hara, H.; Nagaoka, H.; Takahasi, T.; Suzuki, T.; Tomioka, K.; Yamada, T. (Yamanouchi Pharmaceutical Co., Ltd.); Saturated heterocyclic carboxamide derivs.. AU 8812080; EP 0279681; JP 1988208582; US 4987132 .

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(I)	12849	Nicotinaldehyde; 3-Pyridinecarboxaldehyde	500-22-1	C₆H₅NO	详情	详情
(II)	38633	(2S)-2-amino-2-(methylsulfanyl)ethanoic acid		C₃H₇NO₂S	详情	详情
(III)	38634	(4R)-2-(3-pyridinyl)-1,3-thiazolidine-4-carboxylic acid		C₉H₁₀N₂O₂S	详情	详情
(IV)	38637	3-methyl-3-phenylbutyric acid		C₁₁H₁₄O₂	详情	详情
(IV)	38641	1-(3-methyl-3-phenylbutyl)piperazine		C₁₅H₂₄N₂	详情	详情
(V)	38638	3-methyl-3-phenyl-1-butanol		C₁₁H₁₆O	详情	详情
(VI)	38639	1-(3-bromo-1,1-dimethylpropyl)benzene		C₁₁H₁₅Br	详情	详情
(VII)	24694	N-ethoxycarbonylpiperidine; Ethyl 1-piperazinecarboxylate; N-Ethoxycarbonyl piperazine; N-Carbethoxy piperazine	120-43-4	C₇H₁₄N₂O₂	详情	详情
(VIII)	38640	ethyl 4-(3-methyl-3-phenylbutyl)-1-piperazinecarboxylate		C₁₈H₂₈N₂O₂	详情	详情

Extended Information