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【结 构 式】 
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【分子编号】29272 【品名】tert-butyl 2-[5-(tert-butyl)-1H-indol-3-yl]ethylcarbamate 【CA登记号】 |
【 分 子 式 】C19H28N2O2 【 分 子 量 】316.4436 【元素组成】C 72.12% H 8.92% N 8.85% O 10.11% |
合成路线1
该中间体在本合成路线中的序号：(X)Diazotization of 4-tert-butylaniline (I) with NaNO2 and HCl, followed by reduction of the resulting diazonium salt with SnCl2 provided hydrazine (II). Fisher indolization with 4-chlorobutyraldehyde (IV), (obtained by hydrogenation of acid chloride (III)), then afforded tryptamine (V). In an alternative procedure, 4-phthalimidobutyraldehyde diethyl acetal (VIII) was prepared by treatment of amine (VI) with N-carbethoxyphthalimide (VII). Fisher reaction of (VII) with hydrazine (II) produced the (phthalimidoethyl)indole (IX), which was deprotected with hydrazine to furnish the corresponding tryptamine (V). Subsequent condensation of (V) with di-tert-butyl dicarbonate gave carbamate (X). This was finally reduced by means of LiAlH4 providing the target N-methyl tryptamine.
| 【1】 Xu, Y.-C.; Schaus, J.M.; Walker, C.; Krushinski, J.; Adhamm, N.; Zgombick, J.M.; Liang, S.X.; Kohlman, D.T.; Audia, J.E.; N-Methyl-5-tert-butyltryptamine: A novel, highly potent 5-HT1D receptor agonist. J Med Chem 1999, 42, 3, 526. |
| 【2】 Audia, J.E.; Cohen, M.L.; Gidda, J.S.; Nelson, D.L.G.; Baker, S.R.; Ezquerra-Carrera, J.; Lamas-Peteira, C.; Pedregal-Tercero, C. (Eli Lilly and Company); Method for treating 5HT2B receptor related conditions. EP 0749313; JP 1997510216; US 5663178; WO 9524200; WO 9624351 . |
| 【3】 Audia, J.E.; et al. (Eli Lilly and Company); Intermediates to tetrahydro-beta-carbolines. US 5635528 . |
| 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) | 27492 | 4-(tert-butyl)aniline | 769-92-6 | C10H15N | 详情 | 详情 |
| (II) | 29269 | 1-[4-(tert-butyl)phenyl]hydrazine | C10H16N2 | 详情 | 详情 | |
| (III) | 11265 | 4-Chlorobutanoyl chloride; 4-Chlorobutyric acid chloride | 4635-59-0 | C4H6Cl2O | 详情 | 详情 |
| (IV) | 23428 | 4-Chlorobutanal | C4H7ClO | 详情 | 详情 | |
| (V) | 29270 | 2-[5-(tert-butyl)-1H-indol-3-yl]-1-ethanamine | C14H20N2 | 详情 | 详情 | |
| (VI) | 23323 | 4,4-diethoxybutylamine; 4,4-diethoxy-1-butanamine | 6346-09-4 | C8H19NO2 | 详情 | 详情 |
| (VII) | 10283 | ethyl 1,3-dioxo-1,3-dihydro-2H-isoindole-2-carboxylate; N-Carbethoxyphthalimide | 22509-74-6 | C11H9NO4 | 详情 | 详情 |
| (VIII) | 23325 | 2-(4,4-diethoxybutyl)-1H-isoindole-1,3(2H)-dione | C16H21NO4 | 详情 | 详情 | |
| (IX) | 29271 | 2-[2-[5-(tert-butyl)-1H-indol-3-yl]ethyl]-1H-isoindole-1,3(2H)-dione | C22H22N2O2 | 详情 | 详情 | |
| (X) | 29272 | tert-butyl 2-[5-(tert-butyl)-1H-indol-3-yl]ethylcarbamate | C19H28N2O2 | 详情 | 详情 |