Dimethylformamide → 1-(Methylcarbonyloxy-methyl)-5-(1-acenaphthyl)-spiro[indoline-3,4'-piperidin]-2-one

HRID 1441679노트

반응식

HRID 1441679 반응식
Br[CH:2]1[C:12]2=[C:13]3[C:8](=[CH:9][CH:10]=[CH:11]2)[CH:7]=[CH:6][CH:5]=[C:4]3[CH2:3]1.COC([CH2:18][N:19]1[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[C:21]2([CH2:26][CH2:25][NH:24][CH2:23][CH2:22]2)[C:20]1=[O:33])=O.[C:34](=[O:37])([O-])[O-:35].[K+].[K+].[CH3:40]N(C)C=O>>[CH3:40][C:34]([O:35][CH2:18][N:19]1[C:32]2[C:27](=[CH:28][C:29]([CH:2]3[C:12]4=[C:13]5[C:8](=[CH:9][CH:10]=[CH:11]4)[CH:7]=[CH:6][CH:5]=[C:4]5[CH2:3]3)=[CH:30][CH:31]=2)[C:21]2([CH2:22][CH2:23][NH:24][CH2:25][CH2:26]2)[C:20]1=[O:33])=[O:37]

참가 물질

5

반응물 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 136344461-Bromo-acenaphtheneHCID 591645371-(Methoxycarbonylmethyl)-spiro[indoline-3,4'-piperidin]-2-one

생성물 1

HCID 685451281-(Methylcarbonyloxy-methyl)-5-(1-acenaphthyl)-spiro[indoline-3,4'-piperidin]-2-one

실험 절차

1-Bromo-acenaphthene (0.022 g, 0.093 mmol) and 1-(methoxycarbonylmethyl)-spiro[indoline-3,4′-piperidin]-2-one (0.013 g, 0.046 mmol) were dissolved in dry N,N-dimethylformamide (1 mL). Potassium carbonate (0.02 g, 0.14 mmol) was then added and the reaction mixture was stirred at room temperature under a nitrogen atmosphere for 18 hours. The reaction mixture was partitioned with water and ethyl acetate. The organic layer was washed with brine, dried with Na2SO4, filtered and the solvent evaporated in vacuo to yield a crude oil. The crude oil was purified via flash chromatography (5% methanol/dichloromethane) to yield the title compound as a foam.

후처리

  1. customThe reaction mixture was partitioned with water and ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried with Na2SO4
  4. filtrationfiltered
  5. customthe solvent evaporated in vacuo
  6. customto yield a crude oil
  7. customThe crude oil was purified via flash chromatography (5% methanol/dichloromethane)

출처 및 근거

ORD 기록
ord-b4863591d39542a7abd8812fb145e4ff
출처 데이터셋
uspto-grants-2010_02
특허 번호
US07655670B2

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