1-Piperidinecarboxaldehyde → HCID 23518589, compound

HRID 1836874Notes

Reaction equation

HRID 1836874 reaction equation
Br[C:2]1[C:11]([CH2:12][CH2:13][CH2:14][O:15][Si:16]([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:18])[CH3:17])=[CH:10][C:9]2[C:8]([CH3:24])([CH3:23])[CH2:7][CH2:6][C:5]([CH3:26])([CH3:25])[C:4]=2[CH:3]=1.[Li]CCCC.[CH:32](N1CCCCC1)=[O:33]>O1CCCC1>[CH:32]([C:2]1[C:11]([CH2:12][CH2:13][CH2:14][O:15][Si:16]([C:19]([CH3:22])([CH3:20])[CH3:21])([CH3:18])[CH3:17])=[CH:10][C:9]2[C:8]([CH3:24])([CH3:23])[CH2:7][CH2:6][C:5]([CH3:25])([CH3:26])[C:4]=2[CH:3]=1)=[O:33]

Participants

5

Reactant 3

HCID 174291-PiperidinecarboxaldehydeHCID 23518554HCID 23518554, compoundHCID 178418339Butyllithium

Product 1

HCID 23518589HCID 23518589, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 14 g (32 mmol) of 2-bromo-3-(3-t-butyldimethylsiloxypropyl)-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalene in 200 mL of dry tetrahydrofuran at −78° C. was added 24.9 mL (64 mmol) of n-BuLi (2.5 M in hexane) via syringe under N2 atmosphere. The reaction mixture was stirred at this condition for 1 hour. Then it was quenched with a solution of 7 mL (64 mmol) of N-formyl piperidine in 10 mL of dry tetrahydrofuran. The resulting solution was stirred for an additional 30 minutes, when it was quenched with 100 mL of NH4Cl solution. The reaction mixture was extracted with 3×100 mL of ethyl acetate. The organic layers were combined, dried over MgSO4 and the solvent was removed under reduced pressure. The residue was purified by flash chromatography on silica gel (gradient elution: 30% ethyl acetate/hexanes) to afford 11.1 g (90%) of 2-formyl-3-(3-t-butyldimethylsiloxypropyl)-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalene. (M+=386).

Workup

  1. stirringThe resulting solution was stirred for an additional 30 minutes
  2. customwhen it was quenched with 100 mL of NH4Cl solution
  3. extractionThe reaction mixture was extracted with 3×100 mL of ethyl acetate
  4. dry with materialdried over MgSO4
  5. customthe solvent was removed under reduced pressure
  6. customThe residue was purified by flash chromatography on silica gel (gradient elution: 30% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-d2a181f91b854d958de2fd5281c17229
Source dataset
uspto-grants-2004_08
Patent number
US06777418B2

Reaction notes

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