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

HRID 571979Notes

Reaction equation

HRID 571979 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

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%)

Workup

  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

Sources & evidence

ORD record
ord-89fb5b9d7633410faa025e4b9a90a699
Source dataset
uspto-grants-2015_05
Patent number
US09029378B2

Reaction notes

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