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

HRID 1599655Notes

Reaction equation

HRID 1599655 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 it vacuo to give the title compound, (3.01 g, 90%).

Workup

  1. concentrationconcentrated it vacuo

Sources & evidence

ORD record
ord-fe47616626e448f8bea6215d6813e90f
Source dataset
uspto-grants-1998_04
Patent number
US05741799

Reaction notes

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