m-Chloroperbenzoic acid → HCID 57907387, compound

HRID 243700Notes

Reaction equation

HRID 243700 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]2[CH2:7][CH2:8][CH:9]([C:10]([O:12][CH3:13])=[O:11])[C:2]=12.C1C=C(Cl)C=C(C(OO)=[O:22])C=1>ClCCl>[N+:1]1([O-:22])[CH:6]=[CH:5][CH:4]=[C:3]2[CH2:7][CH2:8][CH:9]([C:10]([O:12][CH3:13])=[O:11])[C:2]=12

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 57907593Methyl 6,7-dihydro-5H-cyclopenta[b]pyridine-7-carboxylate

Product 1

HCID 57907387HCID 57907387, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a cooled (0° C.) solution of 1.53 g (8.47 mmol) of methyl 6,7-dihydro-5H-cyclopenta[b]pyridine-7-carboxylate from step A above in 30 mL of dichloromethane was added 1.61 g (9.31 mmol) of m-CPBA. The solution was allowed to stir for 1 h and then quenched with 50 mL of a saturated aqueous sodium bicarbonate solution. The layers were separated and the aqueous phase extracted with dichloromethane (3×50 mL). The combined organic extracts were washed with brine, dried over magnesium sulfate, filtered and evaporated in vacuo to yield the title compound as a light brown solid that was used without purification. LC-MS: m/z (E/S) 194.2 (MH)+.

Workup

  1. customquenched with 50 mL of a saturated aqueous sodium bicarbonate solution
  2. customThe layers were separated
  3. extractionthe aqueous phase extracted with dichloromethane (3×50 mL)
  4. washThe combined organic extracts were washed with brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-bd50adfa82a34cd7b130e824ec8e114e
Source dataset
uspto-grants-2014_02
Patent number
US08653260B2

Reaction notes

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