• English
  • 简体中文
Login Register
Current Location: Home > Feedback Help Print

【结 构 式】

【分子编号】57879

【品名】(1R)-3-phenyl-3-cyclohexene-1-carboxylic acid

【CA登记号】

【 分 子 式 】C13H14O2

【 分 子 量 】202.25296

【元素组成】C 77.2% H 6.98% O 15.82%

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:(VI)

Swern oxidation of 4-hydroxypiperidine-1-carboxylic acid tert-butyl ester (I) with oxalyl chloride in DMSO/dichloromethane gives the corresponding piperidone (II), which is submitted to a Grignard reaction with [U-14C]phenylmagnesium bromide (III) in THF to yield 4-hydroxy-4-phenylpiperidine-1-carboxylic acid tert-butyl ester (IV). The reaction of (IV) with BF3/Et2O in dichloromethane affords labeled 4-phenyl-1,2,3,6-tetrahydropyridine (V), which is condensed with 3-phenyl-3-cyclohexene-1(R)-carboxylic acid (VI) by means of HOBT, DCC and TEA in ethyl acetate to provide the labeled 1-(3-phenyl-3-cyclohexen-1(R)-yl)-1-(4-phenyl-1,2,3,6-tetrahydropyridin-1-yl)methanone (VII). Finally, this compound is reduced with LiAlH4 and AlCl3 in THF to obtain the target tetrahydropyridine derivative.

1 Ekhato, I.V.; Huang, C.C.; Synthesis of (R)-(+)-1,2,3,6-tetrahydro-4-[U-14C]phenyl-1[(3-phenyl-3-cyclohexenyl-1-yl)methyl]pyridine, a potential antipsychotic agent. J Label Compd Radiopharm 1995, 36, 1, 57.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(I) 18625 tert-butyl 4-hydroxy-1-piperidinecarboxylate C10H19NO3 详情 详情
(II) 18620 tert-butyl 4-oxo-1-piperidinecarboxylate;BOC-Piperidone;N-(tert-Butoxycarbonyl)-4-piperidone; N-Boc-4-piperidone 79099-07-3 C10H17NO3 详情 详情
(II) 45167   C6H5BrMg 详情 详情
(III) 17616 bromo(phenyl)magnesium; Phenyl Magnesium Bromide 100-58-3 C6H5BrMg 详情 详情
(IV) 57878 tert-butyl 4-hydroxy-4-phenyl-1-piperidinecarboxylate C16H23NO3 详情 详情
(IV) 64702 tert-butyl 4-hydroxy-4-phenyl-1-piperidinecarboxylate C16H23NO3 详情 详情
(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
(V) 64703 4-Phenyl-1,2,3,6-tetrahydro-pyridine 10338-69-9 C11H13N 详情 详情
(VI) 57879 (1R)-3-phenyl-3-cyclohexene-1-carboxylic acid C13H14O2 详情 详情
(VII) 54955 [(1R)-3-phenyl-3-cyclohexen-1-yl][4-phenyl-3,6-dihydro-1(2H)-pyridinyl]methanone C24H25NO 详情 详情
(VII) 64704 [(1R)-3-phenyl-3-cyclohexen-1-yl][4-phenyl-3,6-dihydro-1(2H)-pyridinyl]methanone C24H25NO 详情 详情
Extended Information