Borane;tetrahydrofuran → (3,4-Dimethyl-phenyl)-[2-(5-methyl-pyridin-2-yl)-ethyl]-amine

HRID 1094358ノート

反応式

HRID 1094358 の反応式
[CH3:1][C:2]1[CH:3]=[C:4]([NH:9][C:10](=O)[CH2:11][C:12]2[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][N:13]=2)[CH:5]=[CH:6][C:7]=1[CH3:8].B.O1CCCC1>C1COCC1>[CH3:1][C:2]1[CH:3]=[C:4]([NH:9][CH2:10][CH2:11][C:12]2[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][N:13]=2)[CH:5]=[CH:6][C:7]=1[CH3:8]

参加物

4

反応物 2

HCID 2723981Borane;tetrahydrofuranHCID 58007566N-(3,4-Dimethyl-phenyl)-2-(5-methyl-pyridin-2-yl)-acetamide

生成物 1

HCID 58007613(3,4-Dimethyl-phenyl)-[2-(5-methyl-pyridin-2-yl)-ethyl]-amine収率 10.5%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

To a solution of 390 mg (1.5 mmol) N-(3,4-dimethyl-phenyl)-2-(5-methyl-pyridin-2-yl)-acetamide in 8 mL THF under argon at ambient temperature, was added dropwise 3.1 mL (3.1 mmol) of a 1 M borane-tetrahydrofuran solution. The solution was refluxed for 5 hours, cooled to 0° C. and quenched with 7 mL of a 20% NH4Cl solution. The solution was acidified with HCl 5N and stirred at ambient temperature for 1.5 hours. The residue was basified with a sat. NaHCO3 solution, and concentrated. The residue was dissolved in ethylacetate, the aqueous phase was extracted 2 times with ethyl acetate. The combined extracts were dried over Na2SO4, filtered and concentrated in vacuo. The crude oil was purified with flash column chromatography on silica eluting with a gradient formed from heptane and ethylacetate to provide 0.038 g (10%) of the title compound as a yellow oil. MS (m/e): 241.3 [M+H]+.

後処理

  1. temperatureThe solution was refluxed for 5 hours
  2. customquenched with 7 mL of a 20% NH4Cl solution
  3. concentrationconcentrated
  4. dissolutionThe residue was dissolved in ethylacetate
  5. extractionthe aqueous phase was extracted 2 times with ethyl acetate
  6. dry with materialThe combined extracts were dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe crude oil was purified with flash column chromatography on silica eluting with a gradient
  10. customformed from heptane and ethylacetate

出典と根拠

ORDレコード
ord-fa3109e7984946a3bb748c21778eb8a0
出典データセット
uspto-grants-2012_03
特許番号
US08133909B2

反応ノート

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