Thiazolidinedione → HCID 58423146, compound

HRID 1398017Notes

Reaction equation

HRID 1398017 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:21]=O)=[C:6]([N:8]2[CH2:12][CH2:11][C@H:10]([NH:13][C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])[CH2:9]2)[CH:7]=1.[S:23]1[CH2:27][C:26](=[O:28])[NH:25][C:24]1=[O:29].N1CCCCC1>C(O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5](/[CH:21]=[C:27]2/[C:26](=[O:28])[NH:25][C:24](=[O:29])[S:23]/2)=[C:6]([N:8]2[CH2:12][CH2:11][C@H:10]([NH:13][C:14](=[O:20])[O:15][C:16]([CH3:17])([CH3:18])[CH3:19])[CH2:9]2)[CH:7]=1

Participants

5

Reactant 3

HCID 5437ThiazolidinedioneHCID 8082PiperidineHCID 58423110HCID 58423110, compound

Product 1

HCID 58423146HCID 58423146, compoundYield 91.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A 100 mL round bottom flask was charged with a magnetic stir bar, (S)-tert-butyl 1-(5-chloro-2-formylphenyl)pyrrolidin-3-ylcarbamate (Method 78) (1.100 g, 3.39 mmol), thiazolidine-2,4-dione (0.397 g, 3.39 mmol), and ethanol (11.29 ml). Piperidine (0.034 mL, 0.34 mmol) was added and the reaction was heated to reflux for 2 h. Once the reaction was judged to be complete by LCMS, it was allowed to cool to ambient temperature and conc. in vacuo to afford the title compound (1.310 g, 91%) which was used in the next step without further purification; m/z 425.

Workup

  1. additionA 100 mL round bottom flask was charged with a magnetic stir bar
  2. temperaturethe reaction was heated
  3. temperatureto reflux for 2 h

Sources & evidence

ORD record
ord-0593b3ec96e34b3e8f9605dbdb063578
Source dataset
uspto-grants-2014_12
Patent number
US08901307B2

Reaction notes

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