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

【结 构 式】

【分子编号】24428

【品名】2-[(1R,2R,3R,5S)-5-(2-[1,1'-biphenyl]-4-ylethoxy)-3-hydroxy-2-(4-morpholinyl)cyclopentyl]acetaldehyde

【CA登记号】

【 分 子 式 】C25H31NO4

【 分 子 量 】409.52548

【元素组成】C 73.32% H 7.63% N 3.42% O 15.63%

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)

The reaction of bicyclo[3.2.0]hept-2-en-6-one (I) with 1,3-dibromo-5,5-dimethylhydantoin (DBDMH) in acetic acid gives 3-endo-acetoxy-2-exo-bromo-bicyclo[3.2.0]heptan-6-one (II), which is treated with morpholine in dichloromethane to yield 5-endo-acetoxy-7-anti morpholinobicyclo[2.2.l]heptan-2-one (III). Hydrolysis of (III) with NaOH gives the norbornanone (IV), which is alkylated with biphenyl methylbromide under phase transfer catalysis to give 5-endo[(1,1'-biphenyl)-4 yl]methoxy-7-anti-morpholinobicyclo[2.2.1]heptan 2-one (V). Baeyer-Villiger oxidation followed by partial reduction with diisobutylaluminum hydride (Dibal) gives the aldehyde (VI), which is then homologated to the aldehyde (VII) using methoxymethylenetriphenyl phosphorane and subsequent treatment with 2N HCl. Condensation of (VII) with 3 carboxypropyl triphenylphosphorane in tetrahydrofuran affords the acid (VIII). Finally, this compound is oxidized with Jones' reagent.

1 Lumley, P.; AH-23848. Drugs Fut 1986, 11, 2, 85.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(A) 10388 Morpholine 110-91-8 C4H9NO 详情 详情
(A) 24427 6-(2-[1,1'-biphenyl]-4-ylethoxy)-8-(4-morpholinyl)-2-oxabicyclo[3.2.1]octan-3-one C25H29NO4 详情 详情
(I) 24421 (1S,5R)bicyclo[3.2.0]hept-2-en-6-one C7H8O 详情 详情
(II) 24422 3-Acetoxy-2-bromobicyclo[3,2,0]hept-2-en-6-one C8H9BrO 详情 详情
(III) 24424 5(endo)-Acetoxy-7(R)-(4-morpholinyl)bicyclo[2,2,1]heptan-2-one C12H19NO2 详情 详情
(IV) 24425 5-hydroxy-7-(4-morpholinyl)bicyclo[2.2.1]heptan-2-one C11H17NO3 详情 详情
(V) 24426 5-(2-[1,1'-biphenyl]-4-ylethoxy)-7-(4-morpholinyl)bicyclo[2.2.1]heptan-2-one C25H29NO3 详情 详情
(VI) 24428 2-[(1R,2R,3R,5S)-5-(2-[1,1'-biphenyl]-4-ylethoxy)-3-hydroxy-2-(4-morpholinyl)cyclopentyl]acetaldehyde C25H31NO4 详情 详情
(VII) 24429 3-[(1R,2R,3R,5S)-5-(2-[1,1'-biphenyl]-4-ylethoxy)-3-hydroxy-2-(4-morpholinyl)cyclopentyl]propanal C26H33NO4 详情 详情
(VIII) 24431 (E)-6-[(1R,2R,3R,5S)-5-(2-[1,1'-biphenyl]-4-ylethoxy)-3-hydroxy-2-(4-morpholinyl)cyclopentyl]-3-hexenoic acid C29H37NO5 详情 详情
(C) 24430 3-Carboxypropyltriphenylphosphonium bromide C22H23BrO2P 详情 详情
Extended Information