|
【结 构 式】 
|
【分子编号】62265 【品名】tert-butyl (2S)-3-hydroxy-2-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：(XVIII)). The hydroxylation of the double bond of (XIV) by means of (Sia)2BH and H2O2 affords the pentanol (XV), which is treated with MsCl and TEA to provide the mesylate (XVI). The cyclization of (XVI) by means of t-BuOK in THF gives the piperidine (XVII), which is desilylated by means of TBAF to yield the piperidinol (XVIII). The oxidation of (XVIII) by means of DMP affords the piperidinone (XIX), which is treated with O-methylhydroxylamine and pyridine to provide the O-methyloxime (XX). The reduction of (XX) with BH3/THF gives the cis-disubstituted piperidine (XXI), which is submitted to a reductocondensation with 2-methoxybenzaldehyde (XXII) by means of NaBH3CN in methanol to yield the secondary amine (XXIII). Finally, the carbamate group of (XXIII) is cleaved by means of HCl in methanol to provide the target piperidine derivative
| 【1】 Yamazaki, N.; et al.; Enantioselective synthesis of NK-1 receptor antagonists (+)-CP-99,994 and (+)-CP-122,721. Tetrahedron Lett 2002, 43, 44, 7979. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (XIV) | 62261 | tert-butyl (1S)-2-{[tert-butyl(dimethyl)silyl]oxy}-1-phenyl-4-pentenylcarbamate | C22H37NO3Si | 详情 | 详情 | |
| (XV) | 62262 | tert-butyl (1S)-2-{[tert-butyl(dimethyl)silyl]oxy}-5-hydroxy-1-phenylpentylcarbamate | C22H39NO4Si | 详情 | 详情 | |
| (XVI) | 62263 | (5S)-5-[(tert-butoxycarbonyl)amino]-4-{[tert-butyl(dimethyl)silyl]oxy}-5-phenylpentyl methanesulfonate | C23H41NO6SSi | 详情 | 详情 | |
| (XVII) | 62264 | tert-butyl (2S)-3-{[tert-butyl(dimethyl)silyl]oxy}-2-phenyl-1-piperidinecarboxylate | C22H37NO3Si | 详情 | 详情 | |
| (XVIII) | 62265 | tert-butyl (2S)-3-hydroxy-2-phenyl-1-piperidinecarboxylate | C16H23NO3 | 详情 | 详情 | |
| (XIX) | 62266 | tert-butyl (2S)-3-oxo-2-phenyl-1-piperidinecarboxylate | C16H21NO3 | 详情 | 详情 | |
| (XX) | 62267 | tert-butyl (2S)-3-(methoxyimino)-2-phenyl-1-piperidinecarboxylate | C17H24N2O3 | 详情 | 详情 | |
| (XXI) | 31756 | tert-butyl (2S,3S)-3-amino-2-phenyl-1-piperidinecarboxylate | C16H24N2O2 | 详情 | 详情 | |
| (XXII) | 12568 | 2-Methoxybenzaldehyde; o-Methoxybenzaldehyde | 135-02-4 | C8H8O2 | 详情 | 详情 |
| (XXIII) | 31757 | tert-butyl (2S,3S)-3-[(2-methoxybenzyl)amino]-2-phenyl-1-piperidinecarboxylate | C24H32N2O3 | 详情 | 详情 |