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【结 构 式】

【分子编号】54950

【品名】5-oxo-3-phenyl-3-cyclohexene-1-carboxylic acid

【CA登记号】

【 分 子 式 】C13H12O3

【 分 子 量 】216.23648

【元素组成】C 72.21% H 5.59% O 22.2%

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:(XXI)

A further procedure employed the chiral keto acid (XXII) as the key intermediate. The cyclohexenone carboxylic acid (XXI) was synthesized via aldol condensation between 3-benzoylacrylic acid (XIX) and ethyl acetoacetate (XX), followed by cyclization and decarboxylation under Robinson annulation reaction conditions. Resolution of (XXI) to furnish the desired (S)-enantiomer (XXII) was accomplished either via formation of the diastereomeric salts with cinchonidine or, alternatively, by esterification of (XXI) with n-butanol --yielding the isomeric mixture (XXIII)--, followed by enantioselective hydrolysis of the (S)-butyl ester from in the presence of alpha-chymotrypsin. Coupling of keto acid (XXII) with tetrahydropyridine (V) provided keto amide (XXIV). The keto group of (XXIV) was then reduced with NaBH4 to form a diastereomeric mixture of allylic alcohols (XXV), which were further reduced employing NaBH3CN in the presence of ZnCl2 to furnish the target (R)-cyclohexenecarboxamide (XXVI). The amide function of (XXVI) was finally reduced to the title amine by means of LiAlH4 in methyl tert-butyl ether.

1 Butler, D.E.; Wustrow, D.J.; Smith, W.J. III; Gailey, J. (Pfizer Inc.); Improved process for R (+) 1,2,3,6-tetrahydro-4-phenyl-1-[(3-phenyl-3-cyclohexen-1-yl)methyl]pyridine, a central nervous system agent. WO 9608473 .
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(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
(XIX) 28661 (E)-4-oxo-4-phenyl-2-butenoic acid 583-06-2 C10H8O3 详情 详情
(XX) 11819 ethyl acetoacetate; ethyl 3-oxobutanoate;Acetoacetic ester;Ethyl beta-ketobutyrate;ethyl 3-oxobutyrate 141-97-9 C6H10O3 详情 详情
(XXI) 54950 5-oxo-3-phenyl-3-cyclohexene-1-carboxylic acid C13H12O3 详情 详情
(XXII) 54952 (1S)-5-oxo-3-phenyl-3-cyclohexene-1-carboxylic acid C13H12O3 详情 详情
(XXIII) 54951 butyl 5-oxo-3-phenyl-3-cyclohexene-1-carboxylate C17H20O3 详情 详情
(XXIV) 54953 (5S)-3-phenyl-5-{[4-phenyl-3,6-dihydro-1(2H)-pyridinyl]carbonyl}-2-cyclohexen-1-one C24H23NO2 详情 详情
(XXV) 54954 [(1S)-5-hydroxy-3-phenyl-3-cyclohexen-1-yl][4-phenyl-3,6-dihydro-1(2H)-pyridinyl]methanone C24H25NO2 详情 详情
(XXVI) 50955 2-[7-fluoro-4-(2-hydroxyethyl)-2-oxo-1(2H)-quinolinyl]acetamide C13H13FN2O3 详情 详情
Extended Information