Ethyl Acrylate → 3-[3-(1-Amino-1-methyl-ethyl)-phenyl]-2-methylacrylic acid methyl ester

HRID 1785454노트

반응식

HRID 1785454 반응식
Br[C:2]1[CH:3]=[C:4]([C:8]([NH2:11])([CH3:10])[CH3:9])[CH:5]=[CH:6][CH:7]=1.CN([CH:20]1[CH2:25][CH2:24]CCC1)C1CCCCC1.C(P(C(C)(C)C)C(C)(C)C)(C)(C)C.[C:39]([O:43][CH2:44]C)(=[O:42])C=C>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O.O1CCOCC1>[CH3:44][O:43][C:39](=[O:42])[C:25]([CH3:24])=[CH:20][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]([NH2:11])([CH3:10])[CH3:9])[CH:3]=1

참가 물질

8

반응물 4

HCID 8821Ethyl AcrylateHCID 24210N-Methyl dicyclohexylamineHCID 83681Tris(1,1-dimethylethyl)phosphineHCID 130256661-(3-Bromophenyl)-1-methylethylamine

생성물 1

HCID 690673703-[3-(1-Amino-1-methyl-ethyl)-phenyl]-2-methylacrylic acid methyl ester

시약·촉매·용매 3

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 962Water용매HCID 312751,4-Dioxane용매

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온도
80 °C

실험 절차

The mixture of 1-(3-bromo-phenyl)-1-methyl-ethylamine (0.74 g, 3.5 mmol), tris(dibenzylideneacetone)dipalladium (0.19 g, 0.21 mmol), and N-methyldicyclohexylamine (10 mmol) was purged with nitrogen followed by the addition of 1,4-dioxane (7 mL) and tri-tert-butylphospine (85 mg, 0.42 mmol). The mixture was again purged with nitrogen and ethyl acrylate (0.75 mL, 7.0 mmol) was added. The mixture was heated to 80° C. for 1 h, brought to room temperature, poured into water (50 mL) and extracted with ethyl acetate (100 mL). The organic layer was separated, washed again with water, dried over magnesium sulfate, concentrated and chromatographed on silica gel using 0-4% MeOHI/CH2Cl2 to afford yellow oil.

후처리

  1. customwas purged with nitrogen
  2. additionwas added
  3. custombrought to room temperature
  4. extractionextracted with ethyl acetate (100 mL)
  5. customThe organic layer was separated
  6. washwashed again with water
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated
  9. customchromatographed on silica gel using 0-4% MeOHI/CH2Cl2
  10. customto afford yellow oil

출처 및 근거

ORD 기록
ord-82f70b5da0c44140bd1eb2eb0d078c06
출처 데이터셋
uspto-grants-2009_03
특허 번호
US07504403B2

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