Magnesium → cis-1-(1,1-Dimethylethyl) 3-ethyl 4-(4-pyridinyl)-1,3-piperidinedicarboxylate

HRID 337675Notes

Reaction equation

HRID 337675 reaction equation
[N:1]1([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:6][CH2:5][C:4]([C:7]2[CH:12]=[CH:11][N:10]=[CH:9][CH:8]=2)=[C:3]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH2:2]1.[Mg]>CO>[N:10]1[CH:11]=[CH:12][C:7]([C@H:4]2[CH2:5][CH2:6][N:1]([C:18]([O:20][C:21]([CH3:22])([CH3:23])[CH3:24])=[O:19])[CH2:2][C@H:3]2[C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 5462224MagnesiumHCID 669000221-(1,1-Dimethylethyl) 3-ethyl 5,6-dihydro-4,4'-bipyridine-1,3(2H)-dicarboxylate

Product 1

HCID 131732024cis-1-(1,1-Dimethylethyl) 3-ethyl 4-(4-pyridinyl)-1,3-piperidinedicarboxylate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a MeOH solution (0.2 M) of 1-(1,1-dimethylethyl) 3-ethyl 5,6-dihydro-4,4′-bipyridine-1,3(2H)-dicarboxylate (1 eq.) from the previous step was added magnesium turnings (3 eq.). The suspension was evacuated and back-filled with N2. Finally, the reaction mixture was sonicated at RT for 2 h during which the magnesium turnings disappeared. The reaction was then quenched with the addition of EtOAc 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 golden yellow oil.

Workup

  1. customThe suspension was evacuated
  2. additionback-filled with N2
  3. customFinally, the reaction mixture was sonicated at RT for 2 h during which the magnesium turnings
  4. customThe reaction was then quenched with the addition of EtOAc and 1 N aq. NaOH
  5. customThe aqueous layer was separated
  6. extractionback-extracted with EtOAc
  7. washThe combined organic extracts were washed further with water and brine
  8. dry with materialdried over Na2SO4
  9. filtrationfiltered

Sources & evidence

ORD record
ord-fcb22f2990374e28a38468ea60523739
Source dataset
uspto-grants-2014_11
Patent number
US08889714B2

Reaction notes

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