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【结 构 式】

【分子编号】54917

【品名】(6aR,9R,10aR)-9-(hydroxymethyl)-7-methyl-7-propyl-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinolin-7-ium iodide

【CA登记号】

【 分 子 式 】C19H27IN2O

【 分 子 量 】426.34073

【元素组成】C 53.53% H 6.38% I 29.77% N 6.57% O 3.75%

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:(III)

The reaction of dihydrolysergol (I) with propyl iodide (II) in hot sulfolane gives the quaternary salt (III), which is treated with Na2S in the same solvent, yielding the propyl derivative (IV). The reaction of (IV) with mesyl chloride and pyridine affords the corresponding mesylate (V), which is finally treated with commercial Na-S-CH3 in DMF to afford the target methylsulfanyl derivative.

1 Anastasia, L.; et al.; Simple and selective one-pot replacement of the N-methyl group of tertiary amines by quaternization and demethylation with sodium sulfide or potassium thioacetate: An application to the synthesis of pergolide. J Chem Soc - Perkins Trans I 2001, 19, 2398.
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) 10051 [(6aR,9R,10aR)-7-methyl-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinolin-9-yl]methanol; 9,10-Dyhydrosergol 18051-16-6 C16H20N2O 详情 详情
(II) 28758 1-iodopropane 107-08-4 C3H7I 详情 详情
(III) 54917 (6aR,9R,10aR)-9-(hydroxymethyl)-7-methyl-7-propyl-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinolin-7-ium iodide C19H27IN2O 详情 详情
(IV) 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
(V) 54918 [(6aR,9R,10aR)-7-propyl-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinolin-9-yl]methyl methanesulfonate C19H26N2O3S 详情 详情
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