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

HRID 970367Notes

Reaction equation

HRID 970367 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11](=[O:14])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:15][Si:16](Cl)([CH3:18])[CH3:17].C(N(CC)CC)C>CN(C=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH:10]=[C:11]([O:14][Si:16]([CH3:18])([CH3:17])[CH3:15])[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 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

To a solution of 4-oxo-piperidine-1-carboxylic acid tert-butyl ester (1 equiv.) in DMF is added TMSCl (1.5 equiv.) and triethylamine (1.5 equiv.) and the reaction solution is heated at 80° C. After 3 hrs the reaction is allowed to cool to RT and the DMF is removed in vacuo. The remaining residue is dissolved in CH2Cl2 and the solution is washed with 10% NaHCO3, dried over Na2SO4, and concentrated to afford the crude title compound. This is used without further purification.

Workup

  1. temperatureto cool to RT
  2. customthe DMF is removed in vacuo
  3. dissolutionThe remaining residue is dissolved in CH2Cl2
  4. washthe solution is washed with 10% NaHCO3
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-4a7bb8b25e76404bb62a613d764c4cad
Source dataset
uspto-grants-2007_12
Patent number
US07312212B2

Reaction notes

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