Pyridine → phenyl 6,7-dihydro-5H-cyclopenta[b]pyridin-3-ylcarbamate

HRID 571979ノート

反応式

HRID 571979 の反応式
[N:1]1[CH:6]=[C:5]([NH2:7])[CH:4]=[C:3]2[CH2:8][CH2:9][CH2:10][C:2]=12.N1C=CC=CC=1.Cl[C:18]([O:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:19]>C(#N)C>[N:1]1[CH:6]=[C:5]([NH:7][C:18](=[O:19])[O:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:4]=[C:3]2[CH2:8][CH2:9][CH2:10][C:2]=12

参加物

5

反応物 3

HCID 1049PyridineHCID 15891Phenyl chloroformateHCID 106305325H,6H,7H-cyclopenta[b]pyridin-3-amine

生成物 1

HCID 86676321phenyl 6,7-dihydro-5H-cyclopenta[b]pyridin-3-ylcarbamate

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

6,7-Dihydro-5H-cyclopenta[b]pyridin-3-amine (D) (250 mg, 1.86 mmol) was dissolved in acetonitrile. The reaction mixture was added pyridine (0.18 mL, 2.23 mmol) and phenyl chloroformate (0.26 mL, 2.05 mmol) and stirred at room temperature for 3 h under N2. TLC showed complete consumption of starting material. The reaction mixture was diluted with water and extracted with ethyl acetate. The organic part was washed with water and brine. The organic layer was dried over MgSO4 and concentrated under reduced pressure. The crude was purified by column chromatography to give phenyl 6,7-dihydro-5H-cyclopenta[b]pyridin-3-ylcarbamate (E). (372 mg, 78%)

後処理

  1. customconsumption of starting material
  2. additionThe reaction mixture was diluted with water
  3. extractionextracted with ethyl acetate
  4. washThe organic part was washed with water and brine
  5. dry with materialThe organic layer was dried over MgSO4
  6. concentrationconcentrated under reduced pressure
  7. customThe crude was purified by column chromatography

出典と根拠

ORDレコード
ord-89fb5b9d7633410faa025e4b9a90a699
出典データセット
uspto-grants-2015_05
特許番号
US09029378B2

反応ノート

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