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

HRID 1095683Notes

Reaction equation

HRID 1095683 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>[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

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)-carboxylateYield 95%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of t-butyl 4-oxopiperidine-1-carboxylate (52.6 g, 264 mmol) in anhydrous DMF (140 mL) was added TMSCl (40.2 mL, 317 mmol) followed by triethylamine (88.3 mL, 634 mmol). The resulting heterogeneous mixture was warmed to 80° C. and stirred for 16 hours. The cooled mixture was diluted with hexanes (500 mL), washed with saturated NaHCO3 (3×300 mL) and brine (200 mL), then dried over Na2SO4, filtered and concentrated to afford 68 g (95%) of desired product as an oil.

Workup

  1. washwashed with saturated NaHCO3 (3×300 mL) and brine (200 mL)
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-61df773f124943008f81174ded407f7b
Source dataset
uspto-grants-2012_03
Patent number
US08138181B2

Reaction notes

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