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

HRID 708576

Reaction equation

HRID 708576 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-5023e02dadb94ae593cf19c2c54b19cf
Source dataset
uspto-grants-2015_11
Patent number
US09175003B2

Linked notes

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