Triacetoxyperiodinane → 1-Boc-3-fluoro-4-pyrrolidinone

HRID 252091Notes

Reaction equation

HRID 252091 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@@H:33]([OH:35])[C@H:32]([F:36])[CH2:31]1)=[O:29])([CH3:26])([CH3:25])[CH3:24]>ClCCl>[C:23]([O:27][C:28]([N:30]1[CH2:34][C:33](=[O:35])[CH:32]([F:36])[CH2:31]1)=[O:29])([CH3:26])([CH3:24])[CH3:25]

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 57416936(3R,4R)-tert-Butyl 3-fluoro-4-hydroxypyrrolidine-1-carboxylate

Product 1

HCID 451589161-Boc-3-fluoro-4-pyrrolidinone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Cool down a suspension of Dess Martin periodinane (279 mg, 0.65 mmol) in dry dichloromethane (1 mL) under nitrogen with an ice bath and add a solution of trans-3-fluoro-4-hydroxypyrrolidine-1-carboxylic acid tert-butyl ester (90 mg, 0.44 mmol) in dry dichloromethane (1 mL). Stir under nitrogen and allow to warm up to room temperature overnight. Add saturated aqueous sodium hydrogen carbonate, then saturated aqueous sodium thiosulfate and extract with dichloromethane. Combine the organic layers, wash with saturated aqueous sodium chloride, dry (magnesium sulfate) and concentrate to give 3-fluoro-4-oxopyrrolidine-1-carboxylic acid tert-butyl ester which may be used without further purification. Characteristic peaks in the NMR include the proton alpha to the fluorine atom (5.01, 1H, ddd, J=51.52, 7.54, 7.25 Hz).

Workup

  1. extractionAdd saturated aqueous sodium hydrogen carbonate, then saturated aqueous sodium thiosulfate and extract with dichloromethane
  2. washwash with saturated aqueous sodium chloride
  3. dry with materialdry (magnesium sulfate)
  4. concentrationconcentrate

Sources & evidence

ORD record
ord-623a860d6c6b464f8ad397965f8fa691
Source dataset
uspto-grants-2011_01
Patent number
US07868014B2

Reaction notes

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