Chlorotrimethylsilane → Tert-butyl 4-(2-(trimethylsilyloxy)allyl)piperidine-1-carboxylate

HRID 335258Notes

Reaction equation

HRID 335258 reaction equation
[Li+].CC([N-]C(C)C)C.[O:9]=[C:10]([CH3:25])[CH2:11][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.Cl[Si:27]([CH3:30])([CH3:29])[CH3:28].C([O-])(O)=O.[Na+]>C1COCC1>[CH3:28][Si:27]([CH3:30])([CH3:29])[O:9][C:10](=[CH2:25])[CH2:11][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

Participants

6

Reactant 4

HCID 6397ChlorotrimethylsilaneHCID 516892Sodium BicarbonateHCID 2724682Lithium diisopropylamideHCID 12017169Tert-butyl 4-(2-oxopropyl)piperidine-1-carboxylate

Product 1

HCID 66994845Tert-butyl 4-(2-(trimethylsilyloxy)allyl)piperidine-1-carboxylateYield 108.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a cooled (−78° C.) solution of LDA (12.3 mL, 24.6 mmol) in THF (50 mL) was added dropwise over 40 minutes a solution of tert-butyl 4-(2-oxopropyl)piperidine-1-carboxylate (4.95 g, 20.5 mmol) in THF (20 mL). After an additional 25 minutes, chlorotrimethylsilane (5.21 mL, 41.0 mmol) was added dropwise over 20 minutes. After stirring for an hour, the reaction was poured into saturated NaHCO3 and extracted with ether (2×400 mL). The combined ether layers were washed with brine, dried, filtered and concentrated to afford the title compound (6.95 g, 108% yield) which was used as is in the next step.

Workup

  1. extractionextracted with ether (2×400 mL)
  2. washThe combined ether layers were washed with brine
  3. customdried
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-bf909ac08ead4168b866905341c6efb3
Source dataset
uspto-grants-2014_11
Patent number
US08883828B2

Reaction notes

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