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【结 构 式】

【分子编号】58429

【品名】tert-butyl (3S)-3-[(4-methyl-1H-imidazol-1-yl)methyl]-1-piperidinecarboxylate

【CA登记号】

【 分 子 式 】C15H25N3O2

【 分 子 量 】279.38252

【元素组成】C 64.49% H 9.02% N 15.04% O 11.45%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号:(XII)

Reduction of (R)-ethyl nipecotate (VII) with LiAlH4 yields 3-piperidinemethanol (VIII), which is further protected as the N-Boc derivative (IX) by using Boc2O. Treatment of the piperidine alcohol (IX) with p-toluenesulfonyl chloride and pyridine leads to tosylate (X). Condensation of the sodium derivative of 4-methylimidazole (XI) with tosylate (X) gives rise to a mixture of regioisomeric N-alkylated imidazoles, which are chromatographically separated after derivatization with trityl chloride. The desired isomer (XII) is then deprotected under acidic conditions, giving piperidine (XIII). Finally, EDC-mediated coupling between piperidine (XIII) and the piperazinecarboxylic acid (VI) furnishes the title amide.

1 Cooper, A.B.; Girijavallabhan, V.M.; Mallams, A.K.; Doll, R.J.; Kelly, J.M.; Rane, D.F.; Taveras, A.G.; Guzi, T.; Strickland, C.; Chao, J. (Schering Corp.); Farnesyl protein transferase inhibitors. EP 1140904; JP 2002533335; WO 0037458 .
2 Cooper, A.B.; Girijavallabhan, V.M.; Mallams, A.K.; Doll, R.J.; Kelly, J.M.; Rane, D.F.; Taveras, A.G.; Guzi, T.; Strickland, C.; Chao, J. (Schering Corp.); Farnesyl protein transferase inhibitors. US 6362188 .
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(VI) 51595 (2R)-4-[(11S)-8-chloro-6,11-dihydro-5H-benzo[5,6]cyclohepta[1,2-b]pyridin-11-yl]-1-[(cyclohexyloxy)carbonyl]-2-piperazinecarboxylic acid C26H30ClN3O4 详情 详情
(VII) 12453 ethyl (3R)hexahydro-3-pyridinecarboxylate C8H15NO2 详情 详情
(VIII) 57427 (1S)-2,2-dimethylcyclopropanecarbonyl chloride C6H9ClO 详情 详情
(IX) 35221 tert-butyl (3S)-3-(hydroxymethyl)-1-piperidinecarboxylate C11H21NO3 详情 详情
(X) 57428 ethyl 3-ethyl-2-pentenoate C9H16O2 详情 详情
(XI) 51586 4-Methylimidazole; 4-Methyl-1H-imidazole; 4-Methyl Imidazole 822-36-6 C4H6N2 详情 详情
(XII) 58429 tert-butyl (3S)-3-[(4-methyl-1H-imidazol-1-yl)methyl]-1-piperidinecarboxylate C15H25N3O2 详情 详情
(XIII) 58430 (3R)-3-[(4-methyl-1H-imidazol-1-yl)methyl]piperidine C10H17N3 详情 详情
Extended Information