m-Chloroperbenzoic acid → trans-1-(1,1-Dimethylethyl) 3-ethyl 4-(1-oxido-4-pyridinyl)-1,3-piperidinedicarboxylate

HRID 337677Notes

Reaction equation

HRID 337677 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([C@@H:7]2[CH2:12][CH2:11][N:10]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:9][C@H:8]2[C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:3][CH:2]=1.ClC1C=C(C=CC=1)C(OO)=[O:30]>ClCCl>[O-:30][N+:1]1[CH:6]=[CH:5][C:4]([C@@H:7]2[CH2:12][CH2:11][N:10]([C:13]([O:15][C:16]([CH3:17])([CH3:18])[CH3:19])=[O:14])[CH2:9][C@H:8]2[C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 131732025HCID 131732025, compound

Product 1

HCID 131732026trans-1-(1,1-Dimethylethyl) 3-ethyl 4-(1-oxido-4-pyridinyl)-1,3-piperidinedicarboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a dichloromethane solution (0.1 M) of trans-1-(1,1-dimethylethyl) 3-ethyl 4-(4-pyridinyl)-1,3-piperidinedicarboxylate (1 eq.) from the previous step was added 3-chloroperoxybenzoic acid (1 eq.). The resulting colorless solution was stirred at RT for 13 h. The reaction was then quenched with sat. aq. NaHSO3 and 1 N aq. NaOH. The aqueous layer was separated and back-extracted with EtOAc. The combined organic extracts were washed further with water and brine, dried over Na2SO4 and filtered. Concentration of the filtrate in vacuo afforded the title compound as a white solid.

Workup

  1. customThe reaction was then quenched with sat. aq. NaHSO3 and 1 N aq. NaOH
  2. customThe aqueous layer was separated
  3. extractionback-extracted with EtOAc
  4. washThe combined organic extracts were washed further with water and brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered

Sources & evidence

ORD record
ord-8838bd16d13e4328842c768c76c52b30
Source dataset
uspto-grants-2014_11
Patent number
US08889714B2

Reaction notes

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