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

HRID 1080836Notes

Reaction equation

HRID 1080836 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-e0ac4bac0b514f74a0c1b0ea8bdf7032
Source dataset
uspto-grants-1996_12
Patent number
US05583146

Reaction notes

Loading…