3-[(1R,2R)-2-(1-pyrrolidinyl)cyclohexyl]phenol -Drug Synthesis Database

【结构式】

【分子编号】61378

【品名】3-[(1R,2R)-2-(1-pyrrolidinyl)cyclohexyl]phenol

【CA登记号】

【分子式】C₁₆H₂₃NO

【分子量】245.36476

【元素组成】C 78.32% H 9.45% N 5.71% O 6.52%

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：(IV)

A mixture of 2-(3-methoxyphenyl)cyclohexanone (I), pyrrolidine (II) and formic acid is heated at 130-40 C to give cis-2-(3-methoxyphenyl)-1-pyrrolidylcyclohexane (III), which is demethylated with refluxing HBr (47%) giving cis-2-(3-hydroxyphenyl)-1-pyrrolidylcyclohexane (IV). Finally this tertiary amine is quaternized with CH3Br.

参考文献中间体

合成目标

【1】 Castaner, J.; Hopkins, S.J.; RX 72601. Drugs Fut 1976, 1, 6, 304.
【2】 Singh, S.K.; Saibaba, V.; Ravikumar, V.; Rudrawar, S.V.; Daga, P.; Rao, C.S.; Akhila, V.; Hedge, P.; Rao, Y.K.; Synthesis and biological evaluation of 2,3-diarylpyrazines and quinoxalines as selective COX-2 inhibitors. J Pharm Pharmac 1974, 26, 8, 134.
【3】 Lewis, J.W. (Reckitt & Colman Pharmaceuticals); FR 2187296 .

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)	61376	2-(3-Methoxyphenyl)cyclohexanone	15547-89-4	C₁₃H₁₆O₂	详情	详情
(II)	11376	Pyrrolidine	123-75-1	C₄H₉N	详情	详情
(III)	61377	1-[(1R,2R)-2-(3-methoxyphenyl)cyclohexyl]pyrrolidine; methyl 3-[(1R,2R)-2-(1-pyrrolidinyl)cyclohexyl]phenyl ether		C₁₇H₂₅NO	详情	详情
(IV)	61378	3-[(1R,2R)-2-(1-pyrrolidinyl)cyclohexyl]phenol		C₁₆H₂₃NO	详情	详情

Extended Information