Pyridine → HCID 67373615, compound

HRID 1677084Notes

Reaction equation

HRID 1677084 reaction equation
[C:1](Cl)(=[O:5])[C:2](Cl)=[O:3].C(Cl)(Cl)Cl.[F:11][C:12]1[CH:13]=[C:14]([C@H:19]2[NH:23][C@@H:22]([C:24]([OH:27])([CH3:26])[CH3:25])[CH2:21][CH2:20]2)[CH:15]=[CH:16][C:17]=1[F:18].N1C=CC=CC=1>O>[F:11][C:12]1[CH:13]=[C:14]([C@H:19]2[N:23]3[C@@H:22]([C:24]([CH3:25])([CH3:26])[O:27][C:1](=[O:5])[C:2]3=[O:3])[CH2:21][CH2:20]2)[CH:15]=[CH:16][C:17]=1[F:18]

Participants

6

Reactant 4

HCID 1049PyridineHCID 6212ChloroformHCID 65578Oxalyl chlorideHCID 67372280HCID 67372280, compound

Product 1

HCID 67373615HCID 67373615, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Under ice-cooling, oxalyl chloride (713 μL) was added dropwise into a chloroform (70 mL) solution containing 2-[(2R,5S)-5-(3,4-difluorophenyl)pyrrolidine-2-yl]propane-2-ol (1.66 g) and pyridine (10 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 resulting solid was washed with a mixture solvent of ether/heptane (1/1), and the title compound (1.3 g) 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. washthe resulting solid was washed with a mixture solvent of ether/heptane (1/1)

Sources & evidence

ORD record
ord-388d109051ec4000ac4d4c949295c3d3
Source dataset
uspto-grants-2011_08
Patent number
US08008293B2

Reaction notes

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