3-Ethyl-7-methyl-3,7-diazabicyclo[3.3.1]nonan-9-one -Drug Synthesis Database

【结构式】

【分子编号】10929

【品名】3-Ethyl-7-methyl-3,7-diazabicyclo[3.3.1]nonan-9-one

【CA登记号】

【分子式】C₁₀H₁₈N₂O

【分子量】182.2658

【元素组成】C 65.9% H 9.95% N 15.37% O 8.78%

与该中间体有关的原料药合成路线共 2 条

合成路线1 合成路线2

合成路线1

该中间体在本合成路线中的序号：(XV)

2) Hexadeuteroethyl alcohol (IX) is treated with red phosphorus and I2 at reflux temperature to give pentadeuteroethyl iodide (X), which is condensed with potassium phthalimide (XI) in DMF, yielding N-(pentadeuteroethyl)phthalimide (XII). The hydrolysis of (XII) with hydrazine and HCl affords pentadeuteroethylamine (XIII), which is condensed with 1-methylpiperidin-4-one (III) and formaldehyde (XIV) in a Mannich reaction to give 3-methyl-7-(pentadeuteroethyl)-3,7-diazabicyclo[3.3.1]nonan-9-one (XV). The reduction of (XV) with NaBH4 as before yields the diastereomeric mixture (XVI + XVII). Finally, the alpha-isomer (XVI) is condensed with 4-chlorobenzoyl chloride (VIII) as before to give the pentadeuterium-labeled bisaramil.

参考文献中间体

合成目标

【1】 Mlinko, S.; Simon Trompler, E.; Szammer, J.; Synthesis of bisaramil labelled with carbon-14 and deuterium. J Label Compd Radiopharm 1994, 34, 4, 313.

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)	10919	1-Methyl-4-piperidone; 1-Methyltetrahydro-4(1H)-pyridinone; N-Methyl-4-piperidone;1-methylpiperidin-4-one	1445-73-4	C₆H₁₁NO	详情	详情
(VIII)	10295	p-Chlorobenzoyl chloride; 4-Chlorobenzoyl chloride	122-01-0	C₇H₄Cl₂O	详情	详情
(IX)	10924	Ethyl alcohol; Ethanol	1516-08-1	C₂H₆O	详情	详情
(IX)	44687	Ethanol-d6		C₂H₆O	详情	详情
(X)	10925	Iodoethane;ethyl iod	75-03-6	C₂H₅I	详情	详情
(X)	44688	1-iodoethane-d5		C₂H₅I	详情	详情
(XI)	10926	(1,3-Dioxo-1,3-dihydro-2H-isoindol-2-yl)potassium		C₈H₄KNO₂	详情	详情
(XII)	10927	2-Ethyl-1H-isoindole-1,3(2H)-dione	5022-29-7	C₁₀H₉NO₂	详情	详情
(XII)	44689	2-ethyl-1H-isoindole-1,3(2H)-dione		C₁₀H₉NO₂	详情	详情
(XIII)	10928	Ethanamine	75-04-7	C₂H₇N	详情	详情
(XIII)	44690	ethylamine; 1-ethanamine		C₂H₇N	详情	详情
(XV)	10929	3-Ethyl-7-methyl-3,7-diazabicyclo[3.3.1]nonan-9-one		C₁₀H₁₈N₂O	详情	详情
(XV)	44691	3-ethyl-7-methyl-3,7-diazabicyclo[3.3.1]nonan-9-one		C₁₀H₁₈N₂O	详情	详情
(XVI)	10921	3-Ethyl-7-methyl-3,7-diazabicyclo[3.3.1]nonan-9-ol		C₁₀H₂₀N₂O	详情	详情
(XVI)	44692	3-ethyl-7-methyl-3,7-diazabicyclo[3.3.1]nonan-9-ol		C₁₀H₂₀N₂O	详情	详情
(XVII)	10922	3-Ethyl-7-methyl-3,7-diazabicyclo[3.3.1]nonan-9-ol		C₁₀H₂₀N₂O	详情	详情
(XVII)	44693	3-ethyl-7-methyl-3,7-diazabicyclo[3.3.1]nonan-9-ol		C₁₀H₂₀N₂O	详情	详情

合成路线2

该中间体在本合成路线中的序号：(I)

Alkylation of potassium phthalimide (I) with an excess of 1,10-dibromodecane (II) in refluxing acetone afforded N-(10-bromodecyl)phthalimide (III). This was condensed with 6-O-demethylgalanthamine (IV) in the presence of Et3N in boiling acetonitrile to give phthalimidodecyl compound (V). Finally, reaction with N-bromosuccinimide in the presence of azobisisobutyronitrile provided the iminium bromide.

参考文献中间体

合成目标

【1】 Mary, A.; Renko, D.Z.; Guillou, C.; Thal, C.; Potent acetylcholinesterase inhibitors: Design, synthesis, and structure-activity relationships of bis-interacting ligands in the galanthamine series. Bioorg Med Chem 1998, 6, 10, 1835.

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)	10929	3-Ethyl-7-methyl-3,7-diazabicyclo[3.3.1]nonan-9-one		C₁₀H₁₈N₂O	详情	详情
(II)	18615	1,10-dibromodecane	4101-68-2	C₁₀H₂₀Br₂	详情	详情
(III)	18616	2-(10-bromodecyl)-1H-isoindole-1,3(2H)-dione	24566-80-1	C₁₈H₂₄BrNO₂	详情	详情
(IV)	18612	(6R,8aS)-3-methoxy-5,6,9,10,11,12-hexahydro-4aH-[1]benzofuro[3a,3,2-ef][2]benzazepin-6-ol		C₁₆H₁₉NO₃	详情	详情
(V)	18618	2-[10-[(6R,8aS)-6-hydroxy-3-methoxy-5,6,9,10-tetrahydro-4aH-[1]benzofuro[3a,3,2-ef][2]benzazepin-11(12H)-yl]decyl]-1H-isoindole-1,3(2H)-dione		C₃₄H₄₂N₂O₅	详情	详情

Extended Information