Acetic Anhydride → trans Ethyl 1-acetyl-4-(2-hydroxyethyl)-piperidine-2-carboxylate

HRID 345345Notes

Reaction equation

HRID 345345 reaction equation
[C:1](OC(=O)C)(=[O:3])[CH3:2].[OH:8][CH2:9][CH2:10][CH:11]1[CH2:16][CH2:15][NH:14][CH:13]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH2:12]1>N1C=CC=CC=1>[C:1]([N:14]1[CH2:15][CH2:16][C@@H:11]([CH2:10][CH2:9][OH:8])[CH2:12][C@@H:13]1[C:17]([O:19][CH2:20][CH3:21])=[O:18])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 19757829Ethyl 4-(2-hydroxyethyl)piperidine-2-carboxylate

Product 1

HCID 14541466trans Ethyl 1-acetyl-4-(2-hydroxyethyl)-piperidine-2-carboxylate

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

At 0°, 9.4 ml acetic anhydride is added to a stirred solution of 13.5 g of ethyl 4-(2-hydroxyethyl)-piperidine-2-carboxylate in 75 ml pyridine. After stirring at room temperature for 30 minutes the solution is concentrated in vacuo and ethyl acetate (300 ml) is added; the solution is washed twice with 2N hydrochloric acid, once with water and once with saturated sodium bicarbonate, dried over sodium sulfate, filtered and concentrated in vacuo. The residue is dissolved in 100 ml ethanol, 5 g of powdered potassium carbonate is added and the mixture stirred 1 hour at room temperature. The solution is filtered, concentrated in vacuo and purified by flash chromatography using methylene chloride/methanol (95:5) to yield trans ethyl 1-acetyl-4-(2-hydroxyethyl)-piperidine-2-carboxylate.

Workup

  1. concentrationis concentrated in vacuo and ethyl acetate (300 ml)
  2. additionis added
  3. washthe solution is washed twice with 2N hydrochloric acid, once with water and once with saturated sodium bicarbonate
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. dissolutionThe residue is dissolved in 100 ml ethanol
  8. addition5 g of powdered potassium carbonate is added
  9. stirringthe mixture stirred 1 hour at room temperature
  10. filtrationThe solution is filtered
  11. concentrationconcentrated in vacuo
  12. custompurified by flash chromatography

Sources & evidence

ORD record
ord-c84f946da1f1447cbd7cbd642e235bf0
Source dataset
uspto-grants-1991_10
Patent number
US05057506

Reaction notes

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