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

HRID 1634200Notes

Reaction equation

HRID 1634200 reaction equation
[CH3:1][Si:2](Cl)([CH3:4])[CH3:3].C(N(CC)CC)C.[C:13]([N:20]1[CH2:25][CH2:24][CH2:23][CH2:22][C:21]1=O)([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14].CN(C=[O:31])C>>[C:16]([O:15][C:13]([N:20]1[CH2:25][CH:24]=[C:23]([O:31][Si:2]([CH3:4])([CH3:3])[CH3:1])[CH2:22][CH2:21]1)=[O:14])([CH3:19])([CH3:18])[CH3:17]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 6397ChlorotrimethylsilaneHCID 8471TriethylamineHCID 7577838tert-Butyl 2-oxopiperidine-1-carboxylate

Product 1

HCID 10778540tert-Butyl 4-((trimethylsilyl)oxy)-5,6-dihydropyridine-1(2H)-carboxylateYield 62%

Conditions

Temperature
70 °C

Procedure

Trimethylsilyl chloride (25 ml) and triethylamine (50 ml) were added to a stirred solution of N-Boc piperidinone (30 g) in DMF (40 ml) and the mixture was heated at 70° C. for 16 h. The solution was cooled to room temperature and diluted with hexanes (300 ml), the solution was washed with sodium bicarbonate solution (3×100 ml), dried (MgSO4) and evaporated to give a colourless oil. The product was purified on silica eluting with 10% ethyl acetate/hexanes to give the title compound as colourless oil (25 g, 62%).

Workup

  1. temperatureThe solution was cooled to room temperature
  2. washthe solution was washed with sodium bicarbonate solution (3×100 ml)
  3. dry with materialdried (MgSO4)
  4. customevaporated
  5. customto give a colourless oil
  6. customThe product was purified on silica eluting with 10% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-98f44d81448d41609e7578c7dd7cd675
Source dataset
uspto-grants-2003_01
Patent number
US06506773B2

Reaction notes

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