m-Chloroperbenzoic acid → HCID 131732036, compound

HRID 337687Notes

Reaction equation

HRID 337687 reaction equation
[CH3:1][O:2][CH2:3][O:4][C:5]1[CH:6]=[N:7][CH:8]=[CH:9][C:10]=1[C@@H:11]1[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][C@H:12]1[C:24]([O:26][CH2:27][CH3:28])=[O:25].ClC1C=C(C=CC=1)C(OO)=[O:34]>ClCCl>[CH3:1][O:2][CH2:3][O:4][C:5]1[CH:6]=[N+:7]([O-:34])[CH:8]=[CH:9][C:10]=1[C@@H:11]1[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:21])[CH3:22])=[O:18])[CH2:13][C@H:12]1[C:24]([O:26][CH2:27][CH3:28])=[O:25]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 131732035HCID 131732035, compound

Product 1

HCID 131732036HCID 131732036, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a dichloromethane solution (0.1 M) of trans-1-(1,1-dimethylethyl) 3-ethyl 4-(3-{[(methyloxy)methyl]oxy}-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-53606fdcdb2849f198ba889475681551
Source dataset
uspto-grants-2014_11
Patent number
US08889714B2

Reaction notes

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