Chlorotrimethylsilane → Tert-butyl 4-{1-[(trimethylsilyl)oxy]vinyl}piperidine-1-carboxylate

HRID 1804596Notes

Reaction equation

HRID 1804596 reaction equation
[Li+].CC([N-]C(C)C)C.[C:9]([CH:12]1[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14][CH2:13]1)(=[O:11])[CH3:10].[CH3:25][Si:26](Cl)([CH3:28])[CH3:27]>C1COCC1>[CH3:25][Si:26]([CH3:28])([CH3:27])[O:11][C:9]([CH:12]1[CH2:13][CH2:14][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:16][CH2:17]1)=[CH2:10]

Participants

5

Reactant 3

HCID 6397ChlorotrimethylsilaneHCID 2724682Lithium diisopropylamideHCID 109879834-Acetyl-piperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 67972300Tert-butyl 4-{1-[(trimethylsilyl)oxy]vinyl}piperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of LDA in THF (70 mL) under nitrogen atmosphere, cooled to −78° C. via dry ice/acetone bath, was added tert-butyl 4-acetylpiperidine-1-carboxylate (5 g, 22 mmol) in THF (30 mL) dropwise over 30 min. The resulting mixture was stirred for an additional 30 min and then TMSCl (2.81 mL) was added via syringe dropwise over 10 min and the resulting solution stirred for 1 h at −78° C. Quench with saturated sodium bicarbonate (300 mL) and extracted with ether (2×200 mL). Combined the organics, wash with brine, dry over sodium sulfate, filter, and concentrate under vacuum. The compound obtained (6.0 g, 92%) was used for the next reaction without further purification.

Workup

  1. stirringthe resulting solution stirred for 1 h at −78° C
  2. customQuench with saturated sodium bicarbonate (300 mL)
  3. extractionextracted with ether (2×200 mL)
  4. washwash with brine
  5. dry with materialdry over sodium sulfate
  6. filtrationfilter
  7. concentrationconcentrate under vacuum
  8. customThe compound obtained (6.0 g, 92%)
  9. customwas used for the next reaction without further purification

Sources & evidence

ORD record
ord-586d6020c288419283ad23b235d63148
Source dataset
uspto-grants-2013_01
Patent number
US08354403B2

Reaction notes

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