Acetic Anhydride → 5H,6H,7H-cyclopenta(b)pyridin-7-yl acetate

HRID 589186Notes

Reaction equation

HRID 589186 reaction equation
[N+:1]1([O-])[CH:6]=[CH:5][CH:4]=[C:3]2[CH2:7][CH2:8][CH2:9][C:2]=12.[C:11]([O:14]C(=O)C)(=[O:13])[CH3:12]>>[C:11]([O:14][CH:9]1[C:2]2=[N:1][CH:6]=[CH:5][CH:4]=[C:3]2[CH2:7][CH2:8]1)(=[O:13])[CH3:12]

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 131533156,7-Dihydro-5H-cyclopenta[b]pyridine 1-oxide

Product 1

HCID 131533165H,6H,7H-cyclopenta(b)pyridin-7-yl acetate

Conditions

Temperature
100 °C

Procedure

A mixture of 6,7-dihydro-5H-cyclopenta[b]pyridine 1-oxide and acetic anhydride was stirred for 30 minutes at 100° C. Concentrated and added DCM (30 mL). The organic layer was washed with Sat. NaHCO3. The organic layer was dried over sodium sulfate and filtered. The organic layer was concentrated in vacuo and purification of the crude material via Isco (3-5% Methanol/DCM) gave rise to the desired 6,7-dihydro-5H-cyclopenta[b]pyridine-7-yl acetate (900 mg).

Workup

  1. concentrationConcentrated
  2. additionadded DCM (30 mL)
  3. washThe organic layer was washed with Sat. NaHCO3
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationThe organic layer was concentrated in vacuo and purification of the crude material via Isco (3-5% Methanol/DCM)

Sources & evidence

ORD record
ord-38a9ec4fed8c40f5aec92a8dcafb2b54
Source dataset
uspto-grants-2016_01
Patent number
US09227971B2

Reaction notes

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