Dimethylformamide → Ethyl 4-(1,3-dioxoisoindolin-2-yl)-1-(2-oxopropyl)cyclo-hexanecarboxylate

HRID 1944734노트

반응식

HRID 1944734 반응식
[CH2:1]([O:3][C:4]([C:6]1([CH2:23][CH:24]=[CH2:25])[CH2:11][CH2:10][CH:9]([N:12]2[C:20](=[O:21])[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[C:13]2=[O:22])[CH2:8][CH2:7]1)=[O:5])[CH3:2].CN(C=[O:30])C>O.Cl.Cl[Cu].Cl[Pd]Cl>[O:21]=[C:20]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:13](=[O:22])[N:12]1[CH:9]1[CH2:8][CH2:7][C:6]([CH2:23][C:24](=[O:30])[CH3:25])([C:4]([O:3][CH2:1][CH3:2])=[O:5])[CH2:11][CH2:10]1

참가 물질

7

반응물 2

HCID 6228Dimethylformamide2회HCID 672250981-Allyl-4-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-cyclohexanecarboxylic acid ethyl ester2회

생성물 1

HCID 67225170Ethyl 4-(1,3-dioxoisoindolin-2-yl)-1-(2-oxopropyl)cyclo-hexanecarboxylate수율 100%

시약·촉매·용매 4

HCID 24290Palladium Chloride촉매HCID 62652Cuprous chloride촉매HCID 313Hydrochloric Acid용매HCID 962Water용매2회

실험 절차

A mixture of CuCl (147 mg, 1.484 mmol) and PdCl2 (46.1 mg, 0.26 mmol) in DMF (24 ml) and water (4 ml) was stirred under an oxygen (balloon) for 3 hours. A solution of 1-Allyl-4-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-cyclohexanecarboxylic acid ethyl ester (Intermediate 73, 362 mg, 1.06 mmol) in DMF (16 ml) was added and the mixture was stirred at room temperature for 66 hr under O2. LCMS shows 100% conversion to product and the reaction mixture was diluted with water and 1M HCl, then extracted with ethyl acetate (×3). The organic layers were washed with water, brine, dried (MgSO4), filtered and concentrated in vacuo to give the title compound as a yellow oil (410 mg, >100%) which was taken to the next step without further purification. LCMS [M+H]=358.3

후처리

  1. stirringthe mixture was stirred at room temperature for 66 hr under O2
  2. extractionextracted with ethyl acetate (×3)
  3. washThe organic layers were washed with water, brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-8de3185c1a0644d3969fb81af0b6c560
출처 데이터셋
uspto-grants-2013_03
특허 번호
US08394858B2

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