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【结 构 式】

【分子编号】38657

【品名】2,2,2-trichloroethyl 5-([[(2,2,2-trichloroethoxy)carbonyl]oxy]methyl)-7-oxa-3-azabicyclo[4.1.0]heptane-3-carboxylate

【CA登记号】

【 分 子 式 】C12H13Cl6NO6

【 分 子 量 】479.95456

【元素组成】C 30.03% H 2.73% Cl 44.32% N 2.92% O 20%

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:(X)

The isomerization of arecoline (I) with LDA gives 1-methyl-1,2,3,6-tetrahydropyridine-3-carboxylic acid methyl ester (II), which is reduced with LiAlH4 in THF yielding the carbinol (III). The protection of (III) with trichloroethyl chloroformate (Troc-Cl) and DIEA in toluene affords the demethylated compound (IV), which is treated with K2CO3 in methanol providing 3-(hydroxymethyl)-1,2,3,6-tetrahydropyridine-1-carboxylic acid 2,2,2-trichloroethyl ester (V). The silylation of (V) with TBDPSCl and imidazole in DMF gives the silyl ether (VI), which is epoxidized with MCPBA in dichloromethane yielding the epoxide (VII). Epoxide (VII) opening by means of HClO4 in refluxing water affords a diastereomeric mixture of racemates (VIII) and (IX) that could not be separated. The cleavage of the carbamate group of (VIII) and (IX) by means of HCl in water gives a new mixture that could be separated by flash chromatography to furnish the target compound as a racemate. Alternatively, intermediate (IV) is epoxidized with MCPBA in dichloromethane yielding the epoxide (X), which is treated as before.

1 Bols, M.; Hansen, S.U.; Synthesis of (±)-isofagomine and its stereoisomers from arecoline. J Chem Soc - Perkins Trans I 2000, 6, 911.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
13664 1,1,1-Trichloro-2-[(chlorocarbonyl)oxy]ethane; 2,2,2-Trichloroethyl chloroformate 17341-93-4 C3H2Cl4O2 详情 详情
(I) 38648 methyl 1-methyl-1,2,5,6-tetrahydro-3-pyridinecarboxylate C8H13NO2 详情 详情
(II) 38649 methyl 1-methyl-1,2,3,6-tetrahydro-3-pyridinecarboxylate C8H13NO2 详情 详情
(III) 38650 (1-methyl-1,2,3,6-tetrahydro-3-pyridinyl)methanol C7H13NO 详情 详情
(IV) 38651 2,2,2-trichloroethyl 3-([[(2,2,2-trichloroethoxy)carbonyl]oxy]methyl)-3,6-dihydro-1(2H)-pyridinecarboxylate C12H13Cl6NO5 详情 详情
(V) 38652 2,2,2-trichloroethyl 3-(hydroxymethyl)-3,6-dihydro-1(2H)-pyridinecarboxylate C9H12Cl3NO3 详情 详情
(VI) 38653 2,2,2-trichloroethyl 3-([[tert-butyl(diphenyl)silyl]oxy]methyl)-3,6-dihydro-1(2H)-pyridinecarboxylate C25H30Cl3NO3Si 详情 详情
(VII) 38654 2,2,2-trichloroethyl 5-([[tert-butyl(diphenyl)silyl]oxy]methyl)-7-oxa-3-azabicyclo[4.1.0]heptane-3-carboxylate C25H30Cl3NO4Si 详情 详情
(VIII) 38655 2,2,2-trichloroethyl (3R,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)-1-piperidinecarboxylate C9H14Cl3NO5 详情 详情
(IX) 38656 2,2,2-trichloroethyl (3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)-1-piperidinecarboxylate C9H14Cl3NO5 详情 详情
(X) 38657 2,2,2-trichloroethyl 5-([[(2,2,2-trichloroethoxy)carbonyl]oxy]methyl)-7-oxa-3-azabicyclo[4.1.0]heptane-3-carboxylate C12H13Cl6NO6 详情 详情
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