【结 构 式】 |
【分子编号】23302 【品名】2,2-diphenylacetyl azide 【CA登记号】 |
【 分 子 式 】C14H11N3O 【 分 子 量 】237.26096 【元素组成】C 70.87% H 4.67% N 17.71% O 6.74% |
合成路线1
该中间体在本合成路线中的序号:(II)Treatment of 2,2-diphenylacetic acid (I) with diphenyl phosphoryl azide (DPPA) yielded acyl azide (II). Then, Curtius rearrangement of (II) in boiling toluene produced the intermediate isocyanate (III), which was coupled with 1-benzyl-4-piperidinol (IV) to afford the corresponding carbamate (V). Subsequent N-debenzylation of (V) was achieved by reaction with 1-chloroethyl chloroformate in refluxing 1,2-dichloroethane, followed by methanolysis to give (VI). Reductive alkylation of (VI) with aldehyde (VII) in the presence of sodium triacetoxyborohydride furnished the substituted benzyl piperidine (VIII). The N-Boc protecting group of (VIII) was finally removed with ethanolic HCl to provide the title compound.
【1】 Naito, R.; Takeuchi, M.; Morihira, K.; Hayakawa, M.; Ikeda, K.; Shibanuma, T.; Isomura, Y.; Selective muscarinic antagonists. I. Synthesis and. Chem Pharm Bull 1998, 46, 8, 1274. |
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) | 19827 | 2,2-diphenylacetic acid | 117-34-0 | C14H12O2 | 详情 | 详情 |
(II) | 23302 | 2,2-diphenylacetyl azide | C14H11N3O | 详情 | 详情 | |
(III) | 23303 | 1-[isocyanato(phenyl)methyl]benzene; benzhydryl isocyanate | C14H11NO | 详情 | 详情 | |
(IV) | 23304 | 1-benzyl-4-piperidinol; 1-benzyl-4-hydroxypiperidine; N-Benzyl-4-hydroxypiperidine; 1-(benzyl)-4-piperidinol | 4727-72-4 | C12H17NO | 详情 | 详情 |
(V) | 23305 | 1-benzyl-4-piperidinyl benzhydrylcarbamate | C26H28N2O2 | 详情 | 详情 | |
(VI) | 23306 | 4-piperidinyl benzhydrylcarbamate | C19H22N2O2 | 详情 | 详情 | |
(VII) | 23307 | tert-butyl 4-formylphenyl(methyl)carbamate | C13H17NO3 | 详情 | 详情 | |
(VIII) | 23308 | 1-[4-[(tert-butoxycarbonyl)(methyl)amino]benzyl]-4-piperidinyl benzhydrylcarbamate | C32H39N3O4 | 详情 | 详情 |