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【结 构 式】 
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【分子编号】57878 【品名】tert-butyl 4-hydroxy-4-phenyl-1-piperidinecarboxylate 【CA登记号】 |
【 分 子 式 】C16H23NO3 【 分 子 量 】277.36356 【元素组成】C 69.29% H 8.36% N 5.05% O 17.31% |
合成路线1
该中间体在本合成路线中的序号：(IV)Swern oxidation of 4-hydroxypiperidine-1-carboxylic acid tert-butyl ester (I) with oxalyl chloride in DMSO/dichloromethane gives the corresponding piperidone (II), which is submitted to a Grignard reaction with [U-14C]phenylmagnesium bromide (III) in THF to yield 4-hydroxy-4-phenylpiperidine-1-carboxylic acid tert-butyl ester (IV). The reaction of (IV) with BF3/Et2O in dichloromethane affords labeled 4-phenyl-1,2,3,6-tetrahydropyridine (V), which is condensed with 3-phenyl-3-cyclohexene-1(R)-carboxylic acid (VI) by means of HOBT, DCC and TEA in ethyl acetate to provide the labeled 1-(3-phenyl-3-cyclohexen-1(R)-yl)-1-(4-phenyl-1,2,3,6-tetrahydropyridin-1-yl)methanone (VII). Finally, this compound is reduced with LiAlH4 and AlCl3 in THF to obtain the target tetrahydropyridine derivative.
| 【1】 Ekhato, I.V.; Huang, C.C.; Synthesis of (R)-(+)-1,2,3,6-tetrahydro-4-[U-14C]phenyl-1[(3-phenyl-3-cyclohexenyl-1-yl)methyl]pyridine, a potential antipsychotic agent. J Label Compd Radiopharm 1995, 36, 1, 57. |
| 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) | 18625 | tert-butyl 4-hydroxy-1-piperidinecarboxylate | C10H19NO3 | 详情 | 详情 | |
| (II) | 18620 | tert-butyl 4-oxo-1-piperidinecarboxylate;BOC-Piperidone;N-(tert-Butoxycarbonyl)-4-piperidone; N-Boc-4-piperidone | 79099-07-3 | C10H17NO3 | 详情 | 详情 |
| (II) | 45167 | C6H5BrMg | 详情 | 详情 | ||
| (III) | 17616 | bromo(phenyl)magnesium; Phenyl Magnesium Bromide | 100-58-3 | C6H5BrMg | 详情 | 详情 |
| (IV) | 57878 | tert-butyl 4-hydroxy-4-phenyl-1-piperidinecarboxylate | C16H23NO3 | 详情 | 详情 | |
| (IV) | 64702 | tert-butyl 4-hydroxy-4-phenyl-1-piperidinecarboxylate | C16H23NO3 | 详情 | 详情 | |
| (V) | 13002 | 4-Phenyl-1,2,3,6-tetrahydropyridine; 1,2,3,6-Tetrahydro-4-phenyl-pyridine | 10338-69-9 | C11H13N | 详情 | 详情 |
| (V) | 64703 | 4-Phenyl-1,2,3,6-tetrahydro-pyridine | 10338-69-9 | C11H13N | 详情 | 详情 |
| (VI) | 57879 | (1R)-3-phenyl-3-cyclohexene-1-carboxylic acid | C13H14O2 | 详情 | 详情 | |
| (VII) | 54955 | [(1R)-3-phenyl-3-cyclohexen-1-yl][4-phenyl-3,6-dihydro-1(2H)-pyridinyl]methanone | C24H25NO | 详情 | 详情 | |
| (VII) | 64704 | [(1R)-3-phenyl-3-cyclohexen-1-yl][4-phenyl-3,6-dihydro-1(2H)-pyridinyl]methanone | C24H25NO | 详情 | 详情 |