4-methoxybicyclo[4.2.0]octa-1,3,5-triene-7-carbonitrile -Drug Synthesis Database

【结构式】

【分子编号】51858

【品名】4-methoxybicyclo[4.2.0]octa-1,3,5-triene-7-carbonitrile

【CA登记号】

【分子式】C₁₀H₉NO

【分子量】159.1876

【元素组成】C 75.45% H 5.7% N 8.8% O 10.05%

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)

Lithiation of 1-cyano-5-methoxybenzocyclobutane (I), followed by addition of cyclohexanone (II), provided the 1-hydroxycyclohexyl adduct (III). The cyano group of (III) was then reduced to amine (IV) using LiAlH4. Reductive alkylation of amine (IV) with formaldehyde and NaBH3CN furnished the corresponding dimethylamino derivative, which was then converted to the corresponding hydrochloride salt with ethereal HCl.

参考文献中间体

合成目标

【1】 Brocco, M.; Harmange, J.-C.; Peglion, J.-L.; Dessinges, A.; Newman-Tancredi, A.; Millan, M. (ADIR et Cie.); Benzocyclobutan cpds., their process for preparation and pharmaceutical compsns. containing them. CA 2264372; EP 0940386; FR 2775687; JP 1999310557; US 6107345 .

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)	51858	4-methoxybicyclo[4.2.0]octa-1,3,5-triene-7-carbonitrile		C₁₀H₉NO	详情	详情
(II)	11059	Cyclohexanone	108-94-1	C₆H₁₀O	详情	详情
(III)	51859	7-(1-hydroxycyclohexyl)-4-methoxybicyclo[4.2.0]octa-1,3,5-triene-7-carbonitrile		C₁₆H₁₉NO₂	详情	详情
(IV)	51860	1-[7-(aminomethyl)-4-methoxybicyclo[4.2.0]octa-1,3,5-trien-7-yl]cyclohexanol		C₁₆H₂₃NO₂	详情	详情

Extended Information