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

HRID 1468000Notes

Reaction equation

HRID 1468000 reaction equation
[O:1]=[C:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][CH2:3]1.[CH3:15][Si:16](Cl)([CH3:18])[CH3:17].C(N(CC)CC)C>CN(C=O)C.CCCCCC>[CH3:15][Si:16]([CH3:18])([CH3:17])[O:1][C:2]1[CH2:3][CH2:4][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:6][CH:7]=1

Participants

6

Reactant 3

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

Product 1

HCID 10778540tert-Butyl 4-((trimethylsilyl)oxy)-5,6-dihydropyridine-1(2H)-carboxylateYield 32%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8058HexaneSolvent

Procedure

To a stirred solution of tert-butyl 4-oxopiperidine-1-carboxylate (5.0 g, 25.0 mmol) in anhydrous DMF (50 mL), trimethylsilyl chloride (3 mL, 30.1 mmol) and triethylamine (8.3 mL, 60.2 mmol) were added at 80° C. and stirred for 10-12 h. The reaction mixture was cooled to room temperature, diluted with hexane and washed with saturated NaHCO3. Combined organic layers were dried over anhydrous Na2SO4, filtered and concentrated in vacuo and the residue was purified by flash column chromatography to give tert-butyl 4-((trimethylsilyl)oxy)-5,6-dihydropyridine-1(2H)-carboxylate as a pale yellow oil (2.16 g, 32%); MS: 271 (M+).

Workup

  1. washwashed with saturated NaHCO3
  2. dry with materialCombined organic layers were dried over anhydrous Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customthe residue was purified by flash column chromatography

Sources & evidence

ORD record
ord-d9c00417eaed4af1bffa4a93a9436f13
Source dataset
uspto-grants-2015_04
Patent number
US09000175B2

Reaction notes

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