m-Chloroperbenzoic acid → HCID 69313017, compound

HRID 1392378Notes

Reaction equation

HRID 1392378 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH:12]=[CH:11][CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].ClC1C=CC=C([C:21](OO)=[O:22])C=1>ClCCl>[O:22]=[C:21]1[CH:10]2[CH:11]1[CH2:12][CH2:13][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[CH2:9]2

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 13094787tert-Butyl 3,6-dihydropyridine-1(2H)-carboxylate

Product 1

HCID 69313017HCID 69313017, compoundYield 142.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To the solution of N-tert-butoxycarbonyl-1,2,3,6-tetrahydropyridine (110 g, 0.60 mol) obtained in Step 1 in 300 ml of dichloromethane, was added 3-chloroperbenzoic acid (m-CPBA; 311 g, 1.80 mol). The reaction mixture was stirred overnight at room temperature and filtered to remove benzoic acid produced. The resulting filtrate was washed with a saturated potassium carbonate solution, brine and distilled water. The resulting organic layer was dried and concentrated on magnesium sulfate to give the titled compound (180.6 g).

Workup

  1. filtrationfiltered
  2. customto remove benzoic acid
  3. customproduced
  4. washThe resulting filtrate was washed with a saturated potassium carbonate solution, brine
  5. distillationdistilled water
  6. customThe resulting organic layer was dried
  7. concentrationconcentrated on magnesium sulfate

Sources & evidence

ORD record
ord-cd642a4907304a7082f65317d3ec0807
Source dataset
uspto-grants-2008_03
Patent number
US07342027B2

Reaction notes

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