Magnesium → HCID 131732029, compound

HRID 337680Notes

Reaction equation

HRID 337680 reaction equation
[CH3:1][C:2]1[C:7]([CH3:8])=[C:6]([C:9]2[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11][C:10]=2[C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH:5]=[C:4]([O:27][CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[N:3]=1.[Mg]>CO>[CH3:1][C:2]1[C:7]([CH3:8])=[C:6]([C@H:9]2[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:19])[CH3:20])=[O:16])[CH2:11][C@H:10]2[C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH:5]=[C:4]([O:27][CH2:28][C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)[N:3]=1

Participants

4

Reactant 2

HCID 5462224MagnesiumHCID 67062149HCID 67062149, compound

Product 1

HCID 131732029HCID 131732029, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a MeOH solution (0.09 M) of 1-(1,1-dimethylethyl) 3-ethyl 2′,3′-dimethyl-6′-[(phenylmethyl)oxy]-5,6-dihydro-4,4′-bipyridine-1,3(2H)-dicarboxylate (1 eq.) from the previous step was added magnesium turnings (3.3 eq.). The suspension was evacuated and back-filled with N2. Finally, the reaction mixture was sonicated at RT for 3 h during which the magnesium turnings disappeared. The reaction was then quenched with the addition of diethyl ether and sat. aq. NH4Cl. The aqueous layer was separated and back-extracted with ether. The combined organic extracts were washed further with water and brine, dried over Na2SO4, filtered and the filtrate concentrated in vacuo. Purification of the crude product thus obtained by way of column chromatography (SiO2, 95:5 (v/v) Hex:EtOAc→1:1 (v/v) Hex:EtOAc) afforded the title compound as a pale yellow oil.

Workup

  1. customThe suspension was evacuated
  2. additionback-filled with N2
  3. customFinally, the reaction mixture was sonicated at RT for 3 h during which the magnesium turnings
  4. customThe reaction was then quenched with the addition of diethyl ether and sat. aq. NH4Cl
  5. customThe aqueous layer was separated
  6. extractionback-extracted with ether
  7. washThe combined organic extracts were washed further with water and brine
  8. dry with materialdried over Na2SO4
  9. filtrationfiltered
  10. concentrationthe filtrate concentrated in vacuo
  11. customPurification of the crude product
  12. customthus obtained by way of column chromatography (SiO2, 95:5 (v/v) Hex:EtOAc→1:1 (v/v) Hex:EtOAc)

Sources & evidence

ORD record
ord-9165a402052f435db24bd689ec158872
Source dataset
uspto-grants-2014_11
Patent number
US08889714B2

Reaction notes

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