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【结 构 式】 
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【分子编号】59284 【品名】tert-butyl 4-(acetylamino)-4-phenyl-1-piperidinecarboxylate 【CA登记号】 |
【 分 子 式 】C18H26N2O3 【 分 子 量 】318.41612 【元素组成】C 67.9% H 8.23% N 8.8% O 15.07% |
合成路线1
该中间体在本合成路线中的序号：(XXXVII)An alternative preparation of the precursor 4-(N-methyl-N-acetyl)amino-4-phenylpiperidine (XXXIX) has been reported. The N-benzyl protecting group of piperidine (III) was replaced with an N-Boc group by catalytic hydrogenolysis to (XXXVI), followed by treatment with Boc2O to yield (XXXVII). Amide (XXXVII) alkylation with iodomethane under phase-transfer conditions gave the N-methyl derivative (XXXVIII). Subsequent N-Boc group cleavage in (XXXVIII) was accomplished by using zinc chloride in CH2Cl2 to afford the piperidine-ZnCl2 complex (XXXIX). This was then alkylated with mesylate (XXVII), and the title compound was finally isolated from the racemic mixture by means of preparative chiral HPLC.
| 【1】 Giardina, G.A.M.; et al.; A reliable and efficient synthesis of SR 142801. Bioorg Med Chem Lett 1996, 6, 19, 2307. |
| 【2】 Grugni, M.; Rigolio, R.; Erhard, K.F. (GlaxoSmithKline Inc.; GlaxoSmithKline SpA); Process for the preparation of 3,3-disubstd. piperidines. WO 9805640 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (III) | 54993 | N-(1-benzyl-4-phenyl-4-piperidinyl)acetamide | C20H24N2O | 详情 | 详情 | |
| (XXVII) | 59278 | 3-[1-benzoyl-3-(3,4-dichlorophenyl)-3-piperidinyl]propyl methanesulfonate | C22H25Cl2NO4S | 详情 | 详情 | |
| (XXXVI) | 59283 | N-(4-phenyl-4-piperidinyl)acetamide | C13H18N2O | 详情 | 详情 | |
| (XXXVII) | 59284 | tert-butyl 4-(acetylamino)-4-phenyl-1-piperidinecarboxylate | C18H26N2O3 | 详情 | 详情 | |
| (XXXVIII) | 59285 | tert-butyl 4-[acetyl(methyl)amino]-4-phenyl-1-piperidinecarboxylate | C19H28N2O3 | 详情 | 详情 | |
| (XXXIX) | 59267 | N-methyl-N-(4-phenyl-4-piperidinyl)acetamide | C14H20N2O | 详情 | 详情 |