6-Cyano-8beta-methoxycarbonylergoline; Methyl (6aR,9R,10aR)-7-cyano-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinoline-9-carboxylate -Drug Synthesis Database

【结构式】

【分子编号】32240

【品名】6-Cyano-8beta-methoxycarbonylergoline; Methyl (6aR,9R,10aR)-7-cyano-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinoline-9-carboxylate

【CA登记号】

【分子式】C₁₇H₁₇N₃O₂

【分子量】295.341

【元素组成】C 69.14% H 5.8% N 14.23% O 10.83%

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：(II)

The reaction of methyl dihydro-lysergate (I) with cyanogen bromide in methylene chloride gives 6-cyano-8beta-methoxycarbonylergoline (II), which is treated with Zn dust and acetic acid - water to afford 8beta-methoxycarbonylergoline (III). The alkylation of (III) with propyl bromide (A) and potassium carbonate in DMF yields 6-n-propyl-8beta-methoxycarbonylergoline (IV), which is reduced with NaBH4 in dioxane - methanol to 6-n-propyl-8beta-hydroxymethylergoline (V). The mesylation of (V) with mesyl chloride in pyridine gives 6-n-propyl-8beta-mesyloxymethylergoline (VI), which is finally treated with sodium methylmercaptide in dimethylacetamide and with methanesulfonic acid.

参考文献中间体

合成目标

【1】 Kornfeld, E.C.; Bach, N.J. (Eli Lilly and Company); 6-N-Propyl-8-methoxymethyl or methylmercaptomethylergolines and related compounds. AT 371817B; DD 141928; EP 0003667; FR 2416891; GB 2014140; US 4166182 .
【2】 Serradell, M.N.; Castaner, J.; Blancafort, P.; Owen, R.T.; Pergolide mesylate. Drugs Fut 1981, 6, 4, 231.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(A)	19502	Propyl bromide; 1-Bromopropane	106-94-5	C₃H₇Br	详情	详情
(I)	32239	Methyl dihydro-lysergate; Methyl (6aR,9R,10aR)-7-methyl-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinoline-9-carboxylate		C₁₇H₂₀N₂O₂	详情	详情
(II)	32240	6-Cyano-8beta-methoxycarbonylergoline; Methyl (6aR,9R,10aR)-7-cyano-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinoline-9-carboxylate		C₁₇H₁₇N₃O₂	详情	详情
(III)	11273	8beta-Methoxycarbonylergoline; Methyl (6aR,9R,10aR)-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinoline-9-carboxylate		C₁₆H₁₈N₂O₂	详情	详情
(IV)	32241	6-n-Propyl-8beta-methoxycarbonylergoline; Methyl (6aR,9R,10aR)-7-propyl-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinoline-9-carboxylate		C₁₉H₂₄N₂O₂	详情	详情
(V)	32242	[(6aR,9R,10aR)-7-propyl-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinolin-9-yl]methanol; 6-n-Propyl-8beta-hydroxymethylergoline		C₁₈H₂₄N₂O	详情	详情
(VI)	32243	6-n-Propyl-8beta-mesyloxymethylergoline; (6aR,9R,10aR)-9-([[Methyl(dimethylene)-lambda(6)-sulfanyl]oxy]methyl)-7-propyl-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinoline		C₂₁H₃₀N₂OS	详情	详情

Extended Information