4,7-Diphenyl-1,10-phenanthroline → Tert-butyl 4-[(vinyloxy)methyl]piperidine-1-carboxylate

HRID 69112Notes

Reaction equation

HRID 69112 reaction equation
[OH:1][CH2:2][CH:3]1[CH2:8][CH2:7][N:6]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:5][CH2:4]1.[C:16]1(C2C3C(=C4C(=CC=3)C(C3C=CC=CC=3)=CC=N4)N=CC=2)C=CC=C[CH:17]=1>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(OC=C)CCC>[CH:16]([O:1][CH2:2][CH:3]1[CH2:8][CH2:7][N:6]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:5][CH2:4]1)=[CH2:17]

Participants

5

Reactant 2

HCID 728124,7-Diphenyl-1,10-phenanthrolineHCID 2764081Tert-butyl 4-(hydroxymethyl)piperidine-1-carboxylate

Product 1

HCID 86694316Tert-butyl 4-[(vinyloxy)methyl]piperidine-1-carboxylateYield 9,182.5%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 8108Butyl vinyl etherSolvent

Procedure

4.3 g of tert-butyl 4-(hydroxymethyl)piperidine-1-carboxylate, 66 mg of 4,7-diphenyl-1,10-phenanthroline, and 45 mg of palladium acetate were added to 50 mL of butylvinyl ether, followed by stirring at room temperature for 15 minutes, and stirring at 75° C. for 2 days. The reaction mixture was filtered through celite, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (n-hexane/ethyl acetate) to obtain 4.4 g of tert-butyl 4-[(vinyloxy)methyl]piperidine-1-carboxylate.

Workup

  1. stirringstirring at 75° C. for 2 days
  2. filtrationThe reaction mixture was filtered through celite
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (n-hexane/ethyl acetate)

Sources & evidence

ORD record
ord-2390eb3d0a4647d3b0b617a4197dcc83
Source dataset
uspto-grants-2014_09
Patent number
US08822448B2

Reaction notes

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