Triethylamine → HCID 86614993, compound

HRID 732352Notes

Reaction equation

HRID 732352 reaction equation
C(N(CC)CC)C.[C:8]([O:12][C:13]([N:15]1[CH2:19][C@@H:18]([F:20])[CH2:17][C@@H:16]1[CH2:21][OH:22])=[O:14])([CH3:11])([CH3:10])[CH3:9]>CS(C)=O.C(OCC)C>[C:8]([O:12][C:13]([N:15]1[CH2:19][C@@H:18]([F:20])[CH2:17][C@@H:16]1[CH:21]=[O:22])=[O:14])([CH3:11])([CH3:10])[CH3:9]

Participants

5

Reactant 2

HCID 8471TriethylamineHCID 58483823tert-Butyl (2R,4S)-4-fluoro-2-(hydroxymethyl)pyrrolidine-1-carboxylate

Product 1

HCID 86614993HCID 86614993, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 3283Diethyl EtherSolvent

Procedure

Add triethylamine (1.1 mL, 7.79 mmol) and sulfurtrioxide-pyridine complex (0.63 g, 3.89 mmol) to an ice-cold solution of 4-(S)-fluoro-2-(R)-hydroxymethylpyrrolidine-1-carboxylic acid tert-butyl ester (0.426 g, 1.95 mmol) in DMSO (2 mL). Stir 30 min, warm to room temperature and stir 30 min. Dilute with diethyl ether and wash with 5% aqueous citric acid (3×120 mL), saturated aqueous sodium chloride, dry (magnesium sulfate) and concentrate to give the title compound as an oil that was used in the next step without further purification.

Workup

  1. stirringstir 30 min
  2. washwash with 5% aqueous citric acid (3×120 mL), saturated aqueous sodium chloride
  3. dry with materialdry (magnesium sulfate)
  4. concentrationconcentrate

Sources & evidence

ORD record
ord-d6b050b86f32492fb28153ddf7687b15
Source dataset
uspto-grants-2009_09
Patent number
US07585885B2

Reaction notes

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