Triethylamine → HCID 86614994, compound

HRID 732359Notes

Reaction equation

HRID 732359 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 68815110HCID 68815110, compound

Product 1

HCID 86614994HCID 86614994, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 3283Diethyl EtherSolvent

Procedure

Add triethylamine (6.6 mL, 47.7 mmol) and sulfurtrioxide-pyridine complex (3.8 g, 23.9 mmol) to an ice cold solution of 4-(R)-fluoro-2-(R)-hydroxymethylpyrrolidine-1-carboxylic acid tert-butyl ester (2.62 g, 11.9 mmol) in DMSO (12 mL). Stir 30 min, then 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 is 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-cd3f5d13c0384f9bb997c03206c4347c
Source dataset
uspto-grants-2009_09
Patent number
US07585885B2

Reaction notes

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