Ethyl Acetate → (E)-(4S*,10aS*)-4-(4-fluorophenyl)-7-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)benzylidene]octahydropyrido[1,2-a]azepin-6-one

HRID 553888노트

반응식

HRID 553888 반응식
O.[OH-].[Li+].[F:4][C:5]1[CH:10]=[CH:9][C:8]([C@@H:11]2[N:16]3[C:17](=[O:30])[CH:18](P(=O)(OCC)OCC)[CH2:19][CH2:20][CH2:21][C@@H:15]3[CH2:14][CH2:13][CH2:12]2)=[CH:7][CH:6]=1.[CH3:31][O:32][C:33]1[CH:34]=[C:35]([CH:38]=[CH:39][C:40]=1[N:41]1[CH:45]=[C:44]([CH3:46])[N:43]=[CH:42]1)[CH:36]=O.C(OCC)(=O)C>O1CCCC1.C(O)C.[Cl-].[Na+].O>[F:4][C:5]1[CH:6]=[CH:7][C:8]([C@H:11]2[N:16]3[C:17](=[O:30])/[C:18](=[CH:36]/[C:35]4[CH:38]=[CH:39][C:40]([N:41]5[CH:45]=[C:44]([CH3:46])[N:43]=[CH:42]5)=[C:33]([O:32][CH3:31])[CH:34]=4)/[CH2:19][CH2:20][CH2:21][C@H:15]3[CH2:14][CH2:13][CH2:12]2)=[CH:9][CH:10]=1

참가 물질

8

반응물 4

HCID 8857Ethyl AcetateHCID 168937Lithium hydroxide, monohydrateHCID 272824453-methoxy-4-(4-methyl-1H-imidazol-1-yl)benzaldehydeHCID 86612698diethyl[(4R*,10aS*)-4-(4-fluorophenyl)-6-oxodecahydropyrido[1,2-a]azepin-7-yl]phosphonate

생성물 1

HCID 24782065(E)-(4S*,10aS*)-4-(4-fluorophenyl)-7-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)benzylidene]octahydropyrido[1,2-a]azepin-6-one수율 50.8%

시약·촉매·용매 3

HCID 702Ethanol용매HCID 8028Tetrahydrofuran용매HCID 57417360Sodium chloride; water용매

실험 절차

Lithium hydroxide monohydrate (68 mg) was added to a mixed solution of diethyl [(4R*,10aS*)-4-(4-fluorophenyl)-6-oxodecahydropyrido[1,2-a]azepin-7-yl]phosphonate (213 mg) and 3-methoxy-4-(4-methyl-1H-imidazol-1-yl)benzaldehyde (116 mg) in tetrahydrofuran (6 mL) and ethanol (1.5 mL), and the reaction solution was stirred at room temperature for 25 hours. Ethyl acetate and brine were added to the reaction solution, and the organic layer was separated. The resulting organic layer was dried over magnesium sulfate and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (carrier: Chromatorex NH; elution solvent: heptane:ethyl acetate=1:1->ethyl acetate) to obtain 125 mg of the title compound. The property values of the compound are as follows.

후처리

  1. customthe organic layer was separated
  2. dry with materialThe resulting organic layer was dried over magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (carrier: Chromatorex NH; elution solvent: heptane:ethyl acetate=1:1->ethyl acetate)

출처 및 근거

ORD 기록
ord-52261e5b94104bfe956e5d8706ed995b
출처 데이터셋
uspto-grants-2011_11
특허 번호
US08048878B2

반응 노트

불러오는 중…