Pyrindan → 6,7-Dihydro-5H-cyclopenta[b]pyridine 1-oxide

HRID 589185

Reaction equation

HRID 589185 reaction equation
ClC1C=C(C=CC=1)C(OO)=[O:6].[CH2:12]1[CH2:16][C:15]2[N:17]=[CH:18][CH:19]=[CH:20][C:14]=2[CH2:13]1>CCOC(C)=O>[N+:17]1([O-:6])[CH:18]=[CH:19][CH:20]=[C:14]2[CH2:13][CH2:12][CH2:16][C:15]=12

Participants

4

Reactant 2

HCID 68292PyrindanHCID 70297m-Chloroperbenzoic acid

Product 1

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

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

3-Chloroperoxybenzoic acid (11.6 g, 67.1 mmol) was dissolved in EtOAc (70 mL, 6 ml/g). The reaction mixture was stirred for 10 minutes at room temperature, and then cooled to 0° C. 2,3-cyclopentenopyridine was dissolved in EtoAc (25 ml, 5 mL/g) which was added dropwise to reaction mixture over 15 minutes keeping the temperature constant below 10° C. The reaction mixture was stirred overnight at ambient temperature. The reaction mixture was quenched with Sat. NaHCO3 (50 mL). The organic layer was dried over sodium sulfate and filtered. Acqu layer was extracted with DCM (40 mL) twice. The organic layer was dried over sodium sulfate and filtered. Combined organic layer was concentrated in vacuo and purification of the crude material via Isco (0-5% Methanol/DCM) gave rise to the desired 6,7-dihydro-5H-cyclopenta[b]pyridine 1-oxide (1.4 g).

Workup

  1. temperaturecooled to 0° C
  2. additionwas added dropwise to reaction mixture over 15 minutes
  3. customthe temperature constant below 10° C
  4. stirringThe reaction mixture was stirred overnight at ambient temperature
  5. customThe reaction mixture was quenched with Sat. NaHCO3 (50 mL)
  6. dry with materialThe organic layer was dried over sodium sulfate
  7. filtrationfiltered
  8. extractionAcqu layer was extracted with DCM (40 mL) twice
  9. dry with materialThe organic layer was dried over sodium sulfate
  10. filtrationfiltered
  11. concentrationCombined organic layer was concentrated in vacuo and purification of the crude material via Isco (0-5% Methanol/DCM)

Sources & evidence

ORD record
ord-571e3f2e607649c095f4255d3f73ce9e
Source dataset
uspto-grants-2016_01
Patent number
US09227971B2

Linked notes

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