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【结 构 式】

【分子编号】13266

【品名】5-(3-Pyridinyl)-4-pentyn-2-ol

【CA登记号】

【 分 子 式 】C10H11NO

【 分 子 量 】161.20348

【元素组成】C 74.51% H 6.88% N 8.69% O 9.92%

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:(X)

B) Synthesis of intermediate (XIV): Palladium-catalyzed coupling of 1-pentyn-4-ol (VIII) with 3-bromopyridine (IX) afforded the pyridinealkynol (X), which was then subjected to sequential hydrogenation and Swern oxidation followed by reductive amination of the intermediate ketone (XI) with sodium cyanoborohyride to afford the racemic amine (XII). Resolution was achieved through fractional crystallization of the corresponding diastereoisomeric (R)-mandelamides that had been obtained by acylation of the racemic amine with (R)-mandelic acid in DMF in the presence of 1-hydroxybenzotriazole and dicyclohexylcarbodiimide. Acid-catalyzed hydrolysis of the diastereoisomerically pure (R,R)-mandelamide (XII) provided the resolved (R)-alpha-methyl-3-pyridinebutanamine (XIV). C) Synthesis of Ro-24-0238: Stereochemical assignment was based on a single crystal X-ray analysis of the intermediate mandelamide. Reaction of the chiral amine with the activated ester of (E,E)-5-(4-methoxyphenyl)-2,4-decadienoic acid gave Ro 24-0238. Stereochemical assignment was based on a single crystal X-ray analysis of the intermediate mandelamide. Reaction of the chiral amine with the activated ester of (E,E)-5-(4-methoxyphenyl)-2,4-decadienoic acid gave Ro 24-0238.

1 Vargaftig, B.B.; Benveniste, J.; Lefort, J.; Wal, F.; Chignard, M.; Background and present status of research on platelet-activating factor (PAF-acether). Ann NY Acad Sci 1981, 370, 119-37.
2 D'Donnell, M.; Kierstead, R.W.; Guthrie, R.W.; Tilley, J.W.; Ro 24-0238. Drugs Fut 1991, 16, 12, 1103.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(VII) 13263 4-nitrophenyl (2E,4E)-5-(4-methoxyphenyl)-2,4-decadienoate C23H25NO5 详情 详情
(VIII) 13264 4-Pentyn-2-ol 2117-11-5 C5H8O 详情 详情
(IX) 13265 3-Bromopyridine 626-55-1 C5H4BrN 详情 详情
(X) 13266 5-(3-Pyridinyl)-4-pentyn-2-ol C10H11NO 详情 详情
(XI) 13267 5-(3-Pyridinyl)-2-pentanone C10H13NO 详情 详情
(XII) 13268 1-Methyl-4-(3-pyridinyl)butylamine; 5-(3-Pyridinyl)-2-pentanamine C10H16N2 详情 详情
(XIII) 13269 (2R)-2-Hydroxy-N-[(1R)-1-methyl-4-(3-pyridinyl)butyl]-2-phenylethanamide C18H22N2O2 详情 详情
(XIV) 13270 (1R)-1-Methyl-4-(3-pyridinyl)butylamine; (2R)-5-(3-Pyridinyl)-2-pentanamine C10H16N2 详情 详情
Extended Information