2-(6,7-dimethyl-1-oxo-1,2,3,4-tetrahydro-2-naphthalenyl)acetic acid -Drug Synthesis Database

【结构式】

【分子编号】41593

【品名】2-(6,7-dimethyl-1-oxo-1,2,3,4-tetrahydro-2-naphthalenyl)acetic acid

【CA登记号】

【分子式】C₁₄H₁₆O₃

【分子量】232.27924

【元素组成】C 72.39% H 6.94% O 20.66%

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：(V)

Mannich reaction of 6,7-dimethyltetralone (I) with dimethylamine and formaldehyde provided amino ketone (II). Subsequent quaternization of (II) with MeI in acetone gave ammonium salt (III), that was further displaced by KCN yielding nitrile (IV). Acidic hydrolysis of the cyano group of (IV) produced carboxylic acid (V). This was then coupled with pyrrolidine (VI) employing BOP reagent to furnish amide (VII). Reduction of the ketone and amide functions of (VII) by means of vitride?in toluene afforded amino alcohol (VIII). After alcohol (VIII) dehydration with ethanolic HCl, the title compound was isolated as the fumarate salt.

参考文献中间体

合成目标

【1】 Kai, N.; Kanehira, A.; Morie, T.; Hino, K.; Kawashima, K.; Shimizu, I.; Akiyama, K. (Dainippon Pharmaceutical Co., Ltd.); 1-[omega-(3,4-Dihydro-2-naphthalenyl)alkyl]cyclic amine derivs., process for producing the same, and medicinal compsn. containing the same. EP 0825180; US 5847159; WO 9633169 .

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)	41589	6,7-dimethyl-3,4-dihydro-1(2H)-naphthalenone		C₁₂H₁₄O	详情	详情
(II)	41590	2-[(dimethylamino)methyl]-6,7-dimethyl-3,4-dihydro-1(2H)-naphthalenone		C₁₅H₂₁NO	详情	详情
(III)	41591	(6,7-dimethyl-1-oxo-1,2,3,4-tetrahydro-2-naphthalenyl)-N,N,N-trimethylmethanaminium iodide		C₁₆H₂₄INO	详情	详情
(IV)	41592	2-(6,7-dimethyl-1-oxo-1,2,3,4-tetrahydro-2-naphthalenyl)acetonitrile		C₁₄H₁₅NO	详情	详情
(V)	41593	2-(6,7-dimethyl-1-oxo-1,2,3,4-tetrahydro-2-naphthalenyl)acetic acid		C₁₄H₁₆O₃	详情	详情
(VI)	11376	Pyrrolidine	123-75-1	C₄H₉N	详情	详情
(VII)	41594	6,7-dimethyl-2-[2-oxo-2-(1-pyrrolidinyl)ethyl]-3,4-dihydro-1(2H)-naphthalenone		C₁₈H₂₃NO₂	详情	详情
(VIII)	41595	6,7-dimethyl-2-[2-(1-pyrrolidinyl)ethyl]-1,2,3,4-tetrahydro-1-naphthalenol		C₁₈H₂₇NO	详情	详情

Extended Information