ethyl 3-ethyl-2-pentenoate -Drug Synthesis Database

【结构式】

【分子编号】57428

【品名】ethyl 3-ethyl-2-pentenoate

【CA登记号】

【分子式】C₉H₁₆O₂

【分子量】156.22484

【元素组成】C 69.19% H 10.32% O 20.48%

与该中间体有关的原料药合成路线共 2 条

合成路线1 合成路线2

合成路线1

该中间体在本合成路线中的序号：(III)

The Wadsworth-Emmons condensation of 3-pentanone (I) with phosphonate (II) affords the conjugated ester adduct (III). Subsequent double bond hydrogenation in (III), in the presence of Pd/C, leads to the saturated ester (IV). After basic hydrolysis of the ethyl ester group of (IV), the resultant carboxylic acid (V) is activated as the corresponding acid chloride (VI) upon treatment with SOCl2. Then, acylation of the silver acetylide of methyl propiolate (VII) with acid chloride (VI) gives rise to the oxo ester intermediate (VIII).

参考文献中间体

合成目标

【1】 Mori, S.; Takechi, S.; Kida, S.; Mizui, T.; Ichihashi, T. (Shionogi & Co. Ltd.); Lignan analog, production thereof, and hypolipidemic drug. EP 0597107; EP 0701991; JP 1993310634; US 5731455; WO 9308155 .

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)	32415	Propione; Dimethylacetone; Diethyl ketone; 3-Pentanone	96-22-0	C₅H₁₀O	详情	详情
(II)	10019	Ethyl 2-(diethoxyphosphoryl)acetate; Triethyl phosphonoacetate	867-13-0	C₈H₁₇O₅P	详情	详情
(III)	57428	ethyl 3-ethyl-2-pentenoate		C₉H₁₆O₂	详情	详情
(IV)	57429	ethyl 3-ethylpentanoate		C₉H₁₈O₂	详情	详情
(V)	57433	3-ethylpentanoic acid		C₇H₁₄O₂	详情	详情
(VI)	57430	3-ethylpentanoyl chloride		C₇H₁₃ClO	详情	详情
(VII)	57431	(3-methoxy-3-oxo-1-propynyl)silver		C₄H₃AgO₂	详情	详情
(VIII)	57432	methyl 6-ethyl-4-oxo-2-octynoate		C₁₁H₁₆O₃	详情	详情

合成路线2

该中间体在本合成路线中的序号：(X)

Reduction of (R)-ethyl nipecotate (VII) with LiAlH4 yields 3-piperidinemethanol (VIII), which is further protected as the N-Boc derivative (IX) by using Boc2O. Treatment of the piperidine alcohol (IX) with p-toluenesulfonyl chloride and pyridine leads to tosylate (X). Condensation of the sodium derivative of 4-methylimidazole (XI) with tosylate (X) gives rise to a mixture of regioisomeric N-alkylated imidazoles, which are chromatographically separated after derivatization with trityl chloride. The desired isomer (XII) is then deprotected under acidic conditions, giving piperidine (XIII). Finally, EDC-mediated coupling between piperidine (XIII) and the piperazinecarboxylic acid (VI) furnishes the title amide.

参考文献中间体

合成目标

【1】 Cooper, A.B.; Girijavallabhan, V.M.; Mallams, A.K.; Doll, R.J.; Kelly, J.M.; Rane, D.F.; Taveras, A.G.; Guzi, T.; Strickland, C.; Chao, J. (Schering Corp.); Farnesyl protein transferase inhibitors. EP 1140904; JP 2002533335; WO 0037458 .
【2】 Cooper, A.B.; Girijavallabhan, V.M.; Mallams, A.K.; Doll, R.J.; Kelly, J.M.; Rane, D.F.; Taveras, A.G.; Guzi, T.; Strickland, C.; Chao, J. (Schering Corp.); Farnesyl protein transferase inhibitors. US 6362188 .

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(VI)	51595	(2R)-4-[(11S)-8-chloro-6,11-dihydro-5H-benzo[5,6]cyclohepta[1,2-b]pyridin-11-yl]-1-[(cyclohexyloxy)carbonyl]-2-piperazinecarboxylic acid		C₂₆H₃₀ClN₃O₄	详情	详情
(VII)	12453	ethyl (3R)hexahydro-3-pyridinecarboxylate		C₈H₁₅NO₂	详情	详情
(VIII)	57427	(1S)-2,2-dimethylcyclopropanecarbonyl chloride		C₆H₉ClO	详情	详情
(IX)	35221	tert-butyl (3S)-3-(hydroxymethyl)-1-piperidinecarboxylate		C₁₁H₂₁NO₃	详情	详情
(X)	57428	ethyl 3-ethyl-2-pentenoate		C₉H₁₆O₂	详情	详情
(XI)	51586	4-Methylimidazole; 4-Methyl-1H-imidazole; 4-Methyl Imidazole	822-36-6	C₄H₆N₂	详情	详情
(XII)	58429	tert-butyl (3S)-3-[(4-methyl-1H-imidazol-1-yl)methyl]-1-piperidinecarboxylate		C₁₅H₂₅N₃O₂	详情	详情
(XIII)	58430	(3R)-3-[(4-methyl-1H-imidazol-1-yl)methyl]piperidine		C₁₀H₁₇N₃	详情	详情

Extended Information