Triethylamine → HCID 53813992, compound

HRID 465362Notes

Reaction equation

HRID 465362 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][C@H:15]([OH:17])[CH2:14][CH2:13][C@H:12]1[C:18]([O:20][CH3:21])=[O:19])=[O:10])[C:2]1C=CC=C[CH:3]=1.ClC(OCC=C)=O.C(N(CC)CC)C.C(OCC)(=O)C>CO.[C].[Pd]>[CH2:1]([O:8][C:9]([N:11]1[CH2:16][C@H:15]([OH:17])[CH2:14][CH2:13][C@H:12]1[C:18]([O:20][CH3:21])=[O:19])=[O:10])[CH:2]=[CH2:3]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 18052Allyl chloroformate2×HCID 140810631-Benzyl 2-methyl (2S,5R)-5-hydroxypiperidine-1,2-dicarboxylate

Product 1

HCID 53813992HCID 53813992, compoundYield 55.9%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

To a solution of 2.46 g (8.39 mmol) of (2S,5R)-1-benzyloxycarbonyl-5-hydroxy-2-methoxycarbonylpiperidine in 100 ml of methanol was added 500 mg of 5% palladium-carbon, and the mixture was hydrogenated for 2 hours at atmospheric pressure and room temperature. The catalyst was removed by filtration, and the filtrate was concentrated. The residue was dissolved in 20 ml of dichloromethane. To this solution was dropwise added 1.3 ml (9.33 mmol) or triethylamine followed by 0.98 ml (9.24 mmol) of allyl chloroformate. After stirring for 2 hours, 1.3 ml (9.33 mmol) of triethylamine and 0.98 ml (9.24 mmol) of allyl chloroformate were additionally added to the mixtures, which was stirred for 1 hours. To the mixture was added 200 ml of ethyl acetate, the organic layer was washed successively with water, 1N potassium bisulfate, water, saturated aqueous sodium bicarbonate, water and saturated aqueous sodium chloride. After drying over anhydrous sodium sulfate, the solvent was removed. The residue was purified by silica gel column chromatography (Wakogel®C-300, elution with ethyl acetate - hexane system) to give 1.14 g (yield: 55 %) of the title compound.

Workup

  1. customThe catalyst was removed by filtration
  2. concentrationthe filtrate was concentrated
  3. dissolutionThe residue was dissolved in 20 ml of dichloromethane
  4. stirringwas stirred for 1 hours
  5. washthe organic layer was washed successively with water, 1N potassium bisulfate, water, saturated aqueous sodium bicarbonate, water and saturated aqueous sodium chloride
  6. dry with materialAfter drying over anhydrous sodium sulfate
  7. customthe solvent was removed
  8. customThe residue was purified by silica gel column chromatography (Wakogel®C-300, elution with ethyl acetate - hexane system)

Sources & evidence

ORD record
ord-43a2f435ff0742fb8a28791020b2d52c
Source dataset
uspto-grants-1992_10
Patent number
US05153188

Reaction notes

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