2-(trimethylsilyl)ethyl 4-oxo-2-vinyl-3,4-dihydropyridine-1(2H)-carboxylate → 2-(Trimethylsilyl)ethyl 4-oxo-2-vinylpiperidine-1-carboxylate

HRID 1510157Notes

Reaction equation

HRID 1510157 reaction equation
[O:1]=[C:2]1[CH:7]=[CH:6][N:5]([C:8]([O:10][CH2:11][CH2:12][Si:13]([CH3:16])([CH3:15])[CH3:14])=[O:9])[CH:4]([CH:17]=[CH2:18])[CH2:3]1>C(O)(=O)C.[Zn]>[O:1]=[C:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][CH2:11][CH2:12][Si:13]([CH3:16])([CH3:15])[CH3:14])=[O:9])[CH:4]([CH:17]=[CH2:18])[CH2:3]1

Participants

4

Reactant 1

HCID 667907952-(trimethylsilyl)ethyl 4-oxo-2-vinyl-3,4-dihydropyridine-1(2H)-carboxylate

Product 1

HCID 667904002-(Trimethylsilyl)ethyl 4-oxo-2-vinylpiperidine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

2-(trimethylsilyl)ethyl 4-oxo-2-vinyl-3,4-dihydropyridine-1(2H)-carboxylate (29.1 g, 109 mmol) in acetic acid (500 ml) was added zinc dust (42.7 g, 652 mmol). The solution stirred at room temperature for 2 hrs and was filtered through a pad of celite. The solvent was evaporated under reduced pressure and the product was purified by column chromatography on silica gel Biotage 65i, eluting with 20% ethyl acetate/hexanes.

Workup

  1. filtrationwas filtered through a pad of celite
  2. customThe solvent was evaporated under reduced pressure
  3. customthe product was purified by column chromatography on silica gel Biotage 65i
  4. washeluting with 20% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-be60c7eb4b2c4fbb9f2843eb49cfc8db
Source dataset
uspto-grants-2012_07
Patent number
US08211904B2

Reaction notes

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