(E)-3-(4-fluorophenyl)-2-propenenitrile -Drug Synthesis Database

【结构式】

【分子编号】56466

【品名】(E)-3-(4-fluorophenyl)-2-propenenitrile

【CA登记号】

【分子式】C₉H₆FN

【分子量】147.1517832

【元素组成】C 73.46% H 4.11% F 12.91% N 9.52%

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：(I)

The condensation of cinnamic nitrile (I) with diethyl malonate (II) by means of K2CO3 and tetrabutylammonium bromide in refluxing acetone or NaOEt in refluxing ethyl acetate gives 2-[2-cyano-1-(4-fluorophenyl)ethyl]malonic acid diethyl ester (III), which is cyclized by reduction of its cyano group with H2 over PtO2 in ethanol/conc. HCl or over Ru/C in ethanol to yield (rac)-(trans)-4-(4-fluorophenyl)-2-oxopiperidine-3-carboxylic acid ethyl ester (IV). Finally, this compound is reduced with NaBH4 in THF to afford (rac)-(trans)-4-(4-fluorophenyl)-3-(hydroxymethyl)piperidine (V), the target intermediate.

参考文献中间体

合成目标

【1】 Dalmases Barjoan, P.; Carulla Oliver, J.M.; Moreno Manas, M.; Perez, M. (Laboratorios Vita, SA); Piperidinone deriv., process for obtaining it and process for using it. ES 2137131 .

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)	56466	(E)-3-(4-fluorophenyl)-2-propenenitrile		C₉H₆FN	详情	详情
(II)	16829	Diethyl malonate	105-53-3	C₇H₁₂O₄	详情	详情
(III)	56467	1-ethyl 3-methyl 2-[2-cyano-1-(4-fluorophenyl)ethyl]malonate		C₁₅H₁₆FNO₄	详情	详情
(IV)	56468	ethyl (3S,4R)-4-(4-fluorophenyl)-2-oxo-3-piperidinecarboxylate		C₁₄H₁₆FNO₃	详情	详情
(V)	43487	[(3S,4R)-4-(4-fluorophenyl)-1-methylpiperidinyl]methanol; trans-(3S)-4-(4-fluorophenyl)-1-methyl-3-piperidine methanol	105812-81-5	C₁₃H₁₈FNO	详情	详情

Extended Information