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

HRID 1785454ノート

反応式

HRID 1785454 の反応式
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

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 962Water溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
80 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-82f70b5da0c44140bd1eb2eb0d078c06
出典データセット
uspto-grants-2009_03
特許番号
US07504403B2

反応ノート

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