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【结 构 式】 
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【分子编号】44356 【品名】tert-butyl 1-(1-cycloocten-1-ylmethyl)-4-piperidinylcarbamate 【CA登记号】 |
【 分 子 式 】C19H34N2O2 【 分 子 量 】322.49124 【元素组成】C 70.76% H 10.63% N 8.69% O 9.92% |
合成路线1
该中间体在本合成路线中的序号：(IV)Cyclooctanone tosylhydrazone was treated with n-BuLi and subsequently reacted with DMF to afford (II). Compound (III) was prepared from 4-tert-butoxycarbonylpiperidine by reductive alkylation with (II). Deprotection of (III) and condensation with 2,7-dichloroxanthen-9-carboxylic acid (IV) using 1,1'-carbonyldiimidazole (CDI) afforded (V). Compound (V) was quaternarized with iodoethane to provide a quaternary ammonium derivative as a mixture of two isomers (cis and trans) attributed to the 4-substituted piperidinium structure in a ratio of 2:1. Finally, the mixture was separated by silica gel column chromatography to give a major isomer, J-113863.
| 【1】 Naya, A.; et al.; Design, synthesis, and discovery of a novel CCR1 antagonist. J Med Chem 2001, 44, 9, 1429. |
| 【2】 Saeki, T.; Naya, A.; J-113863. Drugs Fut 2001, 26, 2, 121. |
| 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) | 14209 | Cyclooctanone | 502-49-8 | C8H14O | 详情 | 详情 |
| (II) | 37975 | 1-cyclooctene-1-carbaldehyde | C9H14O | 详情 | 详情 | |
| (III) | 41601 | tert-butyl 4-piperidinylcarbamate; 4-tert-Boc-aminopiperidine | 73874-95-0 | C10H20N2O2 | 详情 | 详情 |
| (IV) | 44356 | tert-butyl 1-(1-cycloocten-1-ylmethyl)-4-piperidinylcarbamate | C19H34N2O2 | 详情 | 详情 | |
| (V) | 37972 | 2,7-dichloro-9H-xanthene-9-carboxylic acid | C14H8Cl2O3 | 详情 | 详情 | |
| (VI) | 37976 | 2,7-dichloro-N-[1-(1-cycloocten-1-ylmethyl)-4-piperidinyl]-9H-xanthene-9-carboxamide | C28H32Cl2N2O2 | 详情 | 详情 |