Trifluoroacetic acid → Rac-5-isobutylpiperidine-2,4-dione

HRID 1055949Notes

Reaction equation

HRID 1055949 reaction equation
[CH2:1]([CH:5]1[CH2:10][N:9](C(OC(C)(C)C)=O)[C:8](=[O:18])[CH2:7][C:6]1=[O:19])[CH:2]([CH3:4])[CH3:3].C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH2:1]([CH:5]1[CH2:10][NH:9][C:8](=[O:18])[CH2:7][C:6]1=[O:19])[CH:2]([CH3:4])[CH3:3]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 69183944Rac-tert-butyl 5-isobutyl-2,4-dioxopiperidine-1-carboxylate

Product 1

HCID 69180367Rac-5-isobutylpiperidine-2,4-dioneYield 45%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

A mixture of rac-tert-butyl 5-isobutyl-2,4-dioxopiperidine-1-carboxylate (300 mg, 1.115 mmol), DCM (1 mL), and TFA (0.1 mL) was stirred at 25° C. for 2 h. The mixture was concentrated in vacuo and chromatographically purified (basic alumina, 40% EtOAc/petroleum ether) to afford rac-5-isobutylpiperidine-2,4-dione (85 mg, 45% yield) as a pale yellow solid: m/z (ESI, +ve) 170 (M+H)+.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. customchromatographically purified (basic alumina, 40% EtOAc/petroleum ether)

Sources & evidence

ORD record
ord-8aacca1ee7f5489a89531ac0c405b3b7
Source dataset
uspto-grants-2016_07
Patent number
US09394297B2

Reaction notes

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