Dimethylformamide → methyl 3-[1-(phenoxyacetyl)-2,3-dihydro-1H-pyrrol-3-yl]benzoate

HRID 504399노트

반응식

HRID 504399 반응식
N1(C(OC[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=O)CC=CC1.Br[C:17]1[CH:18]=[C:19]([CH:24]=[CH:25][CH:26]=1)[C:20]([O:22][CH3:23])=[O:21].[C:27]([O-:30])(=O)C.[K+].[CH3:32][N:33]([CH3:36])[CH:34]=[O:35].[CH3:37][CH2:38]OC(C)=O>CCCC[N+](CCCC)(CCCC)CCCC.[Br-].O.C([O-])(=O)C.C([O-])(=O)C.[Pd+2]>[O:30]([CH2:27][C:34]([N:33]1[CH:36]=[CH:38][CH:37]([C:17]2[CH:18]=[C:19]([CH:24]=[CH:25][CH:26]=2)[C:20]([O:22][CH3:23])=[O:21])[CH2:32]1)=[O:35])[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

참가 물질

9

반응물 5

HCID 6228DimethylformamideHCID 8857Ethyl AcetateHCID 12070Methyl 3-bromobenzoateHCID 517044Potassium AcetateHCID 643471Benzyl 3-pyrroline-1-carboxylate

생성물 1

HCID 66662462methyl 3-[1-(phenoxyacetyl)-2,3-dihydro-1H-pyrrol-3-yl]benzoate

시약·촉매·용매 3

HCID 74236Tetrabutylammonium Bromide촉매HCID 167845palladium(II) acetate촉매HCID 962Water용매

실험 절차

A solution of benzyl 2,5-dihydro-1H-pyrrole-1-carboxylate (0.626 mL, 0.00349 mol), methyl 3-bromo-benzoate (300 mg, 0.001 mol), palladium(II) diacetate (14 mg, 0.000063 mol), potassium acetate (356 mg, 0.00363 mol), and tetra-N-butylammonium bromide (4.50×10−2 mg, 0.00140 mol) in N,N-dimethylformamide (5 mL, 0.06 mol) was stirred under nitrogen at 40° C. for 4 days. The reaction mixture was diluted with AcOEt and water. The organic layer was separated and the aqueous layer was extracted with AcOEt. The combined organic layer was washed with brine, dried with MgSO4, and concentrated to afford the crude product. The crude product was purified by flash chromatography, eluting with 30% AcOEt in hexanes.

후처리

  1. customThe organic layer was separated
  2. extractionthe aqueous layer was extracted with AcOEt
  3. washThe combined organic layer was washed with brine
  4. dry with materialdried with MgSO4
  5. concentrationconcentrated

출처 및 근거

ORD 기록
ord-508907cfc2de43d58ce1741d2c556de4
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07776874B2

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