m-Chloroperbenzoic acid → Hexahydro-1H-quinolizin-2(6H)-one

HRID 1619369Notes

Reaction equation

HRID 1619369 reaction equation
[CH:1]1[CH:6]=[C:5](Cl)[CH:4]=[C:3]([C:8]([O:10]O)=O)[CH:2]=1.[CH2:12]([N:16]1CCCCC1)[CH2:13]C#C>C(Cl)Cl>[CH2:3]1[CH:2]2[N:16]([CH2:4][CH2:5][CH2:6][CH2:1]2)[CH2:12][CH2:13][C:8]1=[O:10]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acid2×HCID 131559861-(But-3-yn-1-yl)piperidine

Product 1

HCID 2752056Hexahydro-1H-quinolizin-2(6H)-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

m-CPBA (600 mg, 3.65 mmol) was added into a solution of 1-(but-3-ynyl)piperidine (500 mg, 3.65 mmol and 4 Å MS (5× weight of m-CPBA) in DCM under N2 at 0° C. The N-oxide formation was monitored by TLC. After completion, Ph3PAuNTf2 (134 mg, 0.18 mmol) was added to the reaction at 0° C. Upon completion, the mixture was diluted with DCM and the molecular sieves were filtered off. The filtrate was washed with 5% aqueous Na2CO3, dried over Na2SO4 and concentrated under vacuum. The residue was used for the next reaction without further purification. MS (ESI): 154 (MH+).

Workup

  1. additionAfter completion, Ph3PAuNTf2 (134 mg, 0.18 mmol) was added to the reaction at 0° C
  2. filtrationthe molecular sieves were filtered off
  3. washThe filtrate was washed with 5% aqueous Na2CO3
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under vacuum
  6. customThe residue was used for the next reaction without further purification

Sources & evidence

ORD record
ord-a560f90a50b6445cbae285a33e7aa1c5
Source dataset
uspto-grants-2014_07
Patent number
US08772301B2

Reaction notes

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