Methanol → 1-(4-Methoxybenzyl)piperidine-4-carboxaldehyde

HRID 1642109Notes

Reaction equation

HRID 1642109 reaction equation
[H-].C([Al+]CC(C)C)C(C)C.[CH3:11][O:12][C:13]1[CH:29]=[CH:28][C:16]([CH2:17][N:18]2[CH2:23][CH2:22][CH:21]([C:24](OC)=[O:25])[CH2:20][CH2:19]2)=[CH:15][CH:14]=1.CO.[Cl-].[Na+]>C1(C)C=CC=CC=1>[CH3:11][O:12][C:13]1[CH:14]=[CH:15][C:16]([CH2:17][N:18]2[CH2:23][CH2:22][CH:21]([CH:24]=[O:25])[CH2:20][CH2:19]2)=[CH:28][CH:29]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 5234Sodium ChlorideHCID 21225700DiisobutylaluminumhydrideHCID 60704011HCID 60704011, compound

Product 1

HCID 178939301-(4-Methoxybenzyl)piperidine-4-carboxaldehyde

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

A 1.5 M solution of diisobutylaluminium hydride in toluene (3.12 ml, 4.68 mmol) was added dropwise under argon at −78° C., in the course of 30 minutes, to a solution of methyl 1-(4-methoxybenzyl)piperidine-4-carboxylate (1.23 g, 4.68 mmol) in toluene (30 ml), and stirring was then carried out for 30 min at that temperature. Methanol (15 ml) was then added dropwise in such a manner that the internal temperature remained at −78° C., before the mixture was then slowly warmed to room temperature. Saturated sodium chloride solution (20 ml) was added to the reaction mixture, and the suspension was filtered through sea sand. The organic phase was dried over sodium sulfate and concentrated in vacuo. The residue was purified by flash chromatography with cyclohexane/ethyl acetate (1:3).

Workup

  1. customremained at −78° C., before the mixture
  2. filtrationthe suspension was filtered through sea sand
  3. dry with materialThe organic phase was dried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by flash chromatography with cyclohexane/ethyl acetate (1:3)

Sources & evidence

ORD record
ord-4f6801374b354cfeb584e65828f6e94b
Source dataset
uspto-grants-2012_02
Patent number
US08119633B2

Reaction notes

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