1-Piperidinecarboxaldehyde → HCID 178422066, compound

HRID 1836910Notes

Reaction equation

HRID 1836910 reaction equation
[CH2-:1][C:2]([CH3:4])=[O:3].[Br:5][C:6]1[C:15]([CH3:16])=[CH:14][C:13]2[C:12]([CH3:18])([CH3:17])[C@@H:11]([OH:19])[C@@H:10]([OH:20])[C:9]([CH3:22])([CH3:21])[C:8]=2[CH:7]=1.C([Li])CCC.C(N1CCCCC1)=[O:29]>O1CCCC1>[CH2-:1][C:2]([CH3:4])=[O:3].[Br:5][C:6]1[C:15]([CH:16]=[O:29])=[CH:14][C:13]2[C:12]([CH3:18])([CH3:17])[C@H:11]([OH:19])[C@H:10]([OH:20])[C:9]([CH3:22])([CH3:21])[C:8]=2[CH:7]=1

Participants

5

Reactant 3

HCID 174291-PiperidinecarboxaldehydeHCID 178418339ButyllithiumHCID 178421825HCID 178421825, compound

Product 1

HCID 178422066HCID 178422066, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a −78° C. solution of 9.04 g (25.6 mmol) 2-bromo-cis-6,7-dihydroxy-3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphthalene acetonide in 110 ml tetrahydrofuran was added 32.0 ml (51.1 mmol) of a 1.6M solution of n-butyllithium in hexanes. After 1 hour at −78° C., 5.79 g (51.1 mmol) of 1-formylpiperidine was added. After 20 minutes at −78° C., the resulting mixture was quenched with water. Upon warming to room temperature, the mixture was partitioned between ethyl acetate and water. The organic layer was washed with brine, dried over anhydrous sodium sulfate, and concentrated in vacuo. The crude material was purified by flash chromatography with elution with 5% ethyl acetate/hexane to yield 5.65 g (73%) of 3-bromo-cis-6,7-dihydroxy-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthaldehyde acetonide(MH+=303).

Workup

  1. waitAfter 20 minutes at −78° C.
  2. customthe resulting mixture was quenched with water
  3. customthe mixture was partitioned between ethyl acetate and water
  4. washThe organic layer was washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe crude material was purified by flash chromatography with elution with 5% ethyl acetate/hexane

Sources & evidence

ORD record
ord-e6eeddb2236f41c5add128215bec6515
Source dataset
uspto-grants-2004_08
Patent number
US06777418B2

Reaction notes

Loading…