6-hydroxytricyclo[6.2.2.0~2,7~]dodeca-2,4,6-trien-3-yl acetate -Drug Synthesis Database

【结构式】

【分子编号】61075

【品名】6-hydroxytricyclo[6.2.2.0~2,7~]dodeca-2,4,6-trien-3-yl acetate

【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：(VIII)

The selective hydrolysis of 1,4-diacetoxy-5,6,7,8-tetrahydro-5,8-ethanonaphthalene (VII) with diethylamine in methanol gives 4-acetoxy-5,6,7,8-tetrahydro-5,8-ethano-1-naphthol (VIII), which is condensed with epichlorohydrin (III) by means of piperidine at 90 C to afford 1-acetoxy-4-(2,3-epoxypropoxy)-5,6,7,8-tetrahydro-5,8-ethanonaphthalene (VII). The reaction of (IX) with tert-butylamine (V) in refluxing toluene gives 1-acetoxy-4-[3-(tert-butylamino)-2-hydroxypropoxy]-5,6,7,8-tetrahydro-5,8-ethanonaphthalene (X), which is finally hydrolyzed with dry HCl in refluxing methanol

参考文献中间体

合成目标

【1】 Lauria, F.; et al. (Carlo Erba, S.p.A.); BE 790188; CA 992983; CH 565741; DE 2251095; FR 2157897; GB 1351557; JP 7349750; NL 7214106; ZA 7207459 .
【2】 Blancafort, P.; Serradell, M.N.; Castaner, J.; McGillion, F.B.; Nafetolol. Drugs Fut 1981, 6, 2, 92.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(III)	10146	Epichlorohydrin; 2-(Chloromethyl)oxirane	106-89-8	C₃H₅ClO	详情	详情
(V)	17895	2-Amino-2-methylpropane; tert-butylamine; 2-methyl-2-propanamine	75-64-9	C₄H₁₁N	详情	详情
(VII)	61074	6-(acetyloxy)tricyclo[6.2.2.0~2,7~]dodeca-2,4,6-trien-3-yl acetate		C₁₆H₁₈O₄	详情	详情
(VIII)	61075	6-hydroxytricyclo[6.2.2.0~2,7~]dodeca-2,4,6-trien-3-yl acetate		C₁₄H₁₆O₃	详情	详情
(IX)	61076	6-(2-oxiranylmethoxy)tricyclo[6.2.2.0~2,7~]dodeca-2,4,6-trien-3-yl acetate		C₁₇H₂₀O₄	详情	详情
(X)	61077	6-[3-(tert-butylamino)-2-hydroxypropoxy]tricyclo[6.2.2.0~2,7~]dodeca-2,4,6-trien-3-yl acetate		C₂₁H₃₁NO₄	详情	详情

Extended Information