Acetyl chloride → (2S-trans)-4-Methyl-2-piperidinecarboxylic Acid Ethyl Ester

HRID 1599697Notes

Reaction equation

HRID 1599697 reaction equation
[C:1](Cl)(=O)[CH3:2].[CH3:5][C@H:6]1[CH2:11][CH2:10][NH:9][C@H:8]([C:12]([OH:14])=[O:13])[CH2:7]1>CCO>[CH3:5][C@H:6]1[CH2:11][CH2:10][NH:9][C@H:8]([C:12]([O:14][CH2:1][CH3:2])=[O:13])[CH2:7]1

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 44631639(2S,4S)-4-Methylpiperidine-2-carboxylic acid

Product 1

HCID 15697773(2S-trans)-4-Methyl-2-piperidinecarboxylic Acid Ethyl EsterYield 90%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of dry EtOH (65 mL) and acetyl chloride (6.52 mL added dropwise at 0° C.) was added (2S, 4S)-4-methyl pipecolic acid (2.8 g, 19.6 mmol at room temperature. The reaction was stirred at room temperature for 16 hrs and then concentrated in vacuo to give the title compound, (3.01 g, 90%).

Workup

  1. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-582e14faa86a4f2f914917cf9593a981
Source dataset
uspto-grants-1998_04
Patent number
US05741792

Reaction notes

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