Pyridine → HCID 67373169, compound

HRID 1677079Notes

Reaction equation

HRID 1677079 reaction equation
[C:1](Cl)(=[O:5])[C:2](Cl)=[O:3].ClCCl.[F:10][C:11]1[CH:12]=[C:13]([C@H:19]2[NH:23][C@@H:22]([C:24]([OH:27])([CH3:26])[CH3:25])[CH2:21][CH2:20]2)[CH:14]=[C:15]([F:18])[C:16]=1[F:17].N1C=CC=CC=1>O>[CH3:26][C:24]1([CH3:25])[C@H:22]2[CH2:21][CH2:20][C@@H:19]([C:13]3[CH:12]=[C:11]([F:10])[C:16]([F:17])=[C:15]([F:18])[CH:14]=3)[N:23]2[C:2](=[O:3])[C:1](=[O:5])[O:27]1

Participants

6

Reactant 4

HCID 1049PyridineHCID 6344DichloromethaneHCID 65578Oxalyl chlorideHCID 67374271HCID 67374271, compound

Product 1

HCID 67373169HCID 67373169, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Under ice-cooling, oxalyl chloride (320 μL) was added dropwise into a dichloromethane (30 mL) solution containing 2-[(2R,5S)-5-(3,4,5-trifluorophenyl)pyrrolidine-2-yl]propan-2-ol (745 mg) and pyridine (5 mL). After stirring for 30 minutes at the same temperature, water was added to the reaction solution, and the organic layer was partitioned. After washing the organic layer with brine, the resultant was dried over anhydrous magnesium sulfate. The solvent was removed under a vacuum, and the residue was purified by silica gel column chromatography (heptane/ethyl acetate→ethyl acetate), and the title compound (580 mg) was obtained. The physical property values are as follows.

Workup

  1. temperatureUnder ice-cooling
  2. additionwas added to the reaction solution
  3. customthe organic layer was partitioned
  4. washAfter washing the organic layer with brine
  5. dry with materialthe resultant was dried over anhydrous magnesium sulfate
  6. customThe solvent was removed under a vacuum
  7. customthe residue was purified by silica gel column chromatography (heptane/ethyl acetate→ethyl acetate)

Sources & evidence

ORD record
ord-40bf2ff25c6e4e28a15bd9e593c009e5
Source dataset
uspto-grants-2011_08
Patent number
US08008293B2

Reaction notes

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