Triacetoxyperiodinane → 1,1-Dimethylethyl (2S)-4,4-difluoro-2-formyl-1-pyrrolidinecarboxylate

HRID 1644809Notes

Reaction equation

HRID 1644809 reaction equation
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[C:23]([O:27][C:28]([N:30]1[CH2:34][C:33]([F:36])([F:35])[CH2:32][C@H:31]1[CH2:37][OH:38])=[O:29])([CH3:26])([CH3:25])[CH3:24]>C(Cl)Cl>[C:23]([O:27][C:28]([N:30]1[CH2:34][C:33]([F:35])([F:36])[CH2:32][C@H:31]1[CH:37]=[O:38])=[O:29])([CH3:26])([CH3:25])[CH3:24]

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 20648576tert-Butyl (2S)-4,4-difluoro-2-(hydroxymethyl)pyrrolidine-1-carboxylate

Product 1

HCID 866356221,1-Dimethylethyl (2S)-4,4-difluoro-2-formyl-1-pyrrolidinecarboxylateYield 93%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Dess Martin Periodinane (0.9 g, 0.0021 mol) was added in one portion to a solution of (S)-4,4-difluoro-2-hydroxymethyl-pyrrolidine-1-carboxylic acid tert-butyl ester (0.4 g, 0.0016 mol) in DCM (50 mL) under an inert atmosphere. The reaction was stirred until completion (about 2 h) and then quenched with saturated solution of sodium thiosulphate, extracted with DCM (3×100 mL) washed with brine (50 mL), dried over anhydrous sodium sulphate, and concentrated using a rotary evaporator to afford 0.35 g of the desired (S)-4,4-difluoro-2-formyl-pyrrolidine-1-carboxylic acid tert-butyl ester as a light brown colored oil product.

Workup

  1. customquenched with saturated solution of sodium thiosulphate
  2. extractionextracted with DCM (3×100 mL)
  3. washwashed with brine (50 mL)
  4. dry with materialdried over anhydrous sodium sulphate
  5. concentrationconcentrated
  6. customa rotary evaporator

Sources & evidence

ORD record
ord-03206fbef8a142af946b47dce8ad0017
Source dataset
uspto-grants-2012_02
Patent number
US08124636B2

Reaction notes

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