Triacetoxyperiodinane → HCID 58360599, compound

HRID 2194838Notes

Reaction equation

HRID 2194838 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:12][CH:11]([CH2:13][OH:14])[CH2:10][C:9]2=[O:15])=[CH:4][CH:3]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C:9](=[O:15])[CH2:10][CH:11]([CH:13]=[O:14])[CH2:12]2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 104656771-(4-Fluorophenyl)-4-(hydroxymethyl)pyrrolidin-2-one

Product 1

HCID 58360599HCID 58360599, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A 500 mL round-bottomed flask was charged with 1-(4-fluorophenyl)-4-(hydroxymethyl)pyrrolidin-2-one 53 (6.01 g, 28.7 mmol), 100 mL of DCM, and Dess-Martin periodinane (DMP) (15.8 g, 57.3 mmol). After stirring at room temperature for 1.5 h, the reaction was quenched with saturated aqueous sodium thiosulfate and filtered. The layers were separated and the residue was purified by column chromatography on silica gel (10% to 90% EtOAc in hexanes) to give 1-(4-fluorophenyl)-5-oxopyrrolidine-3-carbaldehyde 54.

Workup

  1. customthe reaction was quenched with saturated aqueous sodium thiosulfate
  2. filtrationfiltered
  3. customThe layers were separated
  4. customthe residue was purified by column chromatography on silica gel (10% to 90% EtOAc in hexanes)

Sources & evidence

ORD record
ord-068ae892a4af4591bfbe2be6d4169096
Source dataset
uspto-grants-2012_12
Patent number
US08334317B2

Reaction notes

Loading…