Sodium Hydroxide → HCID 118208808, compound

HRID 595224Notes

Reaction equation

HRID 595224 reaction equation
[OH-].[Na+].[NH2:3][CH2:4][C:5]([CH2:17][N:18]1[CH:22]=[C:21]([I:23])[CH:20]=[N:19]1)([O:12][Si](C)(C)C)[CH2:6][C:7](OCC)=[O:8]>CO.O>[OH:12][C:5]1([CH2:17][N:18]2[CH:22]=[C:21]([I:23])[CH:20]=[N:19]2)[CH2:4][NH:3][C:7](=[O:8])[CH2:6]1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 131734575HCID 131734575, compound

Product 1

HCID 118208808HCID 118208808, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Sodium hydroxide (113 mg, 2.8 mmol) was added to a mixture of ethyl 4-amino-3-((4-iodo-1H-pyrazol-1-yl)methyl)-3-((trimethylsilyl)oxy)butanoate (1.2 g, 2.8 mmol) in methanol (10 mL) and the mixture was stirred at room temperature for 2 hours. The mixture was diluted with water and extracted with DCM. The organic layer was dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by prep-TLC (petroleum ether/EtOAc) to afford 4-hydroxy-4-((4-iodo-1H-pyrazol-1-yl)methyl)pyrrolidin-2-one. MS ESI calc'd. for C8H11IN3O2 [M+H]+ 308. found 308. 1H NMR (400 MHz, CDCl3) δ 7.58 (s, 1H), 7.51 (s, 1H), 4.28 (s, 2H), 3.34 (s, 2H), 2.29-2.05 (m, 2H).

Workup

  1. extractionextracted with DCM
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by prep-TLC (petroleum ether/EtOAc)

Sources & evidence

ORD record
ord-efeecd824ae343df92eddc34a67ef120
Source dataset
uspto-grants-2016_01
Patent number
US09242984B2

Reaction notes

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