Nitrogen → tert-Butyl 4-((trimethylsilyl)oxy)-5,6-dihydropyridine-1(2H)-carboxylate

HRID 2280376Notes

Reaction equation

HRID 2280376 reaction equation
N#N.[O:3]=[C:4]1[CH2:9][CH2:8][N:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:6][CH2:5]1.[CH3:17][Si:18](Cl)([CH3:20])[CH3:19].CCN(CC)CC>CN(C=O)C>[CH3:17][Si:18]([CH3:20])([CH3:19])[O:3][C:4]1[CH2:5][CH2:6][N:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:8][CH:9]=1

Participants

6

Reactant 4

HCID 947NitrogenHCID 6397ChlorotrimethylsilaneHCID 8471TriethylamineHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylate

Product 1

HCID 10778540tert-Butyl 4-((trimethylsilyl)oxy)-5,6-dihydropyridine-1(2H)-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), to a solution of tert-butyl 4-oxopiperidine-1-carboxylate (5.00 g, 25.09 mmol) in dry DMF (25 mL) was added trimethylsilyl chloride (5.77 mL, 45.17 mmol) followed by Et3N (8.38 mL, 60.23 mmol) at rt. The reaction mixture was stirred at 80° C. for 24 h. The mixture was then cooled to rt, diluted with hexanes and washed with sat. aq. NaHCO3. The layers were separated and the org. layer dried over MgSO4, filtered, and concentrated under reduced pressure. The residue was purified by FC (hexanes/EA, 9:1) to afford tert-butyl 4-((trimethylsilyl)oxy)-5,6-dihydropyridine-1(2H)-carboxylate as a colorless oil. Rf (Hexanes/EA, 9:1)=0.50.

Workup

  1. temperatureThe mixture was then cooled to rt
  2. washwashed with sat. aq. NaHCO3
  3. customThe layers were separated
  4. dry with materiallayer dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by FC (hexanes/EA, 9:1)

Sources & evidence

ORD record
ord-7427465e89d2484ab0aa97d34eb3dfca
Source dataset
uspto-grants-2015_09
Patent number
US09139524B2

Reaction notes

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