Triacetoxyperiodinane → 2-(4-Fluoro-phenyl)-2-formyl-pyrrolidine-1-carboxylic acid tert-butyl ester

HRID 1644819Notes

Reaction equation

HRID 1644819 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][C:9]1([C:15]1[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=1)[CH2:13][OH:14])=[O:7])([CH3:4])([CH3:3])[CH3:2].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][C:9]1([C:15]1[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=1)[CH:13]=[O:14])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 667735772-(4-Fluoro-phenyl)-2-hydroxymethyl-pyrrolidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 866356232-(4-Fluoro-phenyl)-2-formyl-pyrrolidine-1-carboxylic acid tert-butyl esterYield 106.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 2-(4-fluoro-phenyl)-2-hydroxymethyl-pyrrolidine-1-carboxylic acid tert-butyl ester (3.9 g) in a round bottom flask was added Dess-Martin periodinane solution (47 mL of a 15% solution in DCM, CAS [87413-09-0]) and the reaction mixture was stirred for 5 hours at RT. The reaction mixture was then quenched with saturated aqueous sodium thiosulfate solution (25 mL) and stirred a further 20 minutes. The phases were separated and the aqueous was extracted with further DCM (25 mL). The combined organic phases were washed with saturated sodium bicarbonate solution and dried over sodium sulfate. Filtration of the drying agent and evaporation of the volatiles in vacuo afforded the desired 2-(4-fluoro-phenyl)-2-formyl-pyrrolidine-1-carboxylic acid tert-butyl ester (4.13 g, MS (ES+): 294.1 (MH+)) as a brown solid which was taken into the next step without further purification.

Workup

  1. customThe reaction mixture was then quenched with saturated aqueous sodium thiosulfate solution (25 mL)
  2. stirringstirred a further 20 minutes
  3. customThe phases were separated
  4. extractionthe aqueous was extracted with further DCM (25 mL)
  5. washThe combined organic phases were washed with saturated sodium bicarbonate solution
  6. dry with materialdried over sodium sulfate
  7. filtrationFiltration of the drying agent and evaporation of the volatiles in vacuo

Sources & evidence

ORD record
ord-0743f584853140efbd7affb7db0cec47
Source dataset
uspto-grants-2012_02
Patent number
US08124636B2

Reaction notes

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