Trifluoroacetic acid → 4-(2-Methoxy-ethyl)-2-oxo-piperidine-4-carboxylic acid ethyl ester

HRID 420649Notes

Reaction equation

HRID 420649 reaction equation
[CH2:1]([O:3][C:4]([C:6]1([CH2:20][CH2:21][O:22][CH3:23])[CH2:11][CH2:10][N:9](C(OC(C)(C)C)=O)[C:8](=[O:19])[CH2:7]1)=[O:5])[CH3:2].FC(F)(F)C(O)=O>ClCCl>[CH2:1]([O:3][C:4]([C:6]1([CH2:20][CH2:21][O:22][CH3:23])[CH2:11][CH2:10][NH:9][C:8](=[O:19])[CH2:7]1)=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 584784134-(2-Methoxy-ethyl)-2-oxo-piperidine-1,4-dicarboxylic acid 1-tert-butyl ester 4-ethyl ester

Product 1

HCID 584784144-(2-Methoxy-ethyl)-2-oxo-piperidine-4-carboxylic acid ethyl esterYield 24.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-(2-Methoxy-ethyl)-2-oxo-piperidine-1,4-dicarboxylic acid 1-tert-butyl ester 4-ethyl ester (8.7 g) dissolved in dichloromethane (300 ml) under an argon atmosphere was treated with trifluoroacetic acid (60.32 g, 39.11 ml) and stirred for 3 hours at RT. The reaction mixture was then concentrated in vacuo, the residue dissolved in AcOEt, which was then washed with 3M aqueous NaOH, brine and dried over magnesium sulphate. The solvent was removed in vacuo and the residue was chromatographed on silica gel (acetone/CH2Cl2, gradient 0 to 10%) to give the desired product as light brown viscous oil (1.49 g). MS (ESI): 230.13 (MH+).

Workup

  1. concentrationThe reaction mixture was then concentrated in vacuo
  2. dissolutionthe residue dissolved in AcOEt
  3. washwhich was then washed with 3M aqueous NaOH, brine
  4. dry with materialdried over magnesium sulphate
  5. customThe solvent was removed in vacuo
  6. customthe residue was chromatographed on silica gel (acetone/CH2Cl2, gradient 0 to 10%)

Sources & evidence

ORD record
ord-b5edc976f5f74b478606338ec24a4bd0
Source dataset
uspto-grants-2012_01
Patent number
US08097634B2

Reaction notes

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