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

HRID 391784

Reaction equation

HRID 391784 reaction equation
[N:1]1[C:9]2[CH2:8][CH2:7][CH2:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.C(OO)(=[O:12])C>C(Cl)Cl>[N+:1]1([O-:12])[C:9]2[CH2:8][CH2:7][CH2:6][C:5]=2[CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 6585Peracetic AcidHCID 68292Pyrindan

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

N-oxide formation also was performed under the following conditions. To a 6,7-dihydro-5H-[1]pyrindine solution in DCM at 0° C. was added peracetic acid (3 mL, 32% in AcOH), and the reaction was slowly allowed to come to rt and stirred for 12 h. The reaction mixture was diluted with DCM (5 mL) and washed with water, aq NaHCO3, brine, then dried over Na2SO4, filtered and concentrated to afford desired 6,7-dihydro-5H-[1]pyrindine 1-oxide (0.6 g). LCMS (m/z): 136.

Workup

  1. customto come to rt
  2. washwashed with water, aq NaHCO3, brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-5f949f76b1e847f79d06363480c08628
Source dataset
uspto-grants-2013_02
Patent number
US08383644B2

Linked notes

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