Pyridine → HCID 67378613, compound

HRID 1677070Notes

Reaction equation

HRID 1677070 reaction equation
[C:1](Cl)(=[O:5])[C:2](Cl)=[O:3].ClCCl.[F:10][C:11]1[CH:16]=[CH:15][C:14]([C@H:17]2[NH:21][C@@H:20]([C@@H:22]([OH:24])[CH3:23])[CH2:19][CH2:18]2)=[CH:13][CH:12]=1.N1C=CC=CC=1>O>[F:10][C:11]1[CH:16]=[CH:15][C:14]([C@H:17]2[N:21]3[C@@H:20]([C@H:22]([CH3:23])[O:24][C:1](=[O:5])[C:2]3=[O:3])[CH2:19][CH2:18]2)=[CH:13][CH:12]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 6344DichloromethaneHCID 65578Oxalyl chlorideHCID 67371742HCID 67371742, compound

Product 1

HCID 67378613HCID 67378613, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Under ice-cooling, oxalyl chloride (392 μL) was added dropwise into a dichloromethane (4 mL) solution containing (S)-1-[(2R,5S)-5-(4-fluorophenyl)pyrrolidine-2-yl]ethanol (479 mg) and pyridine (1 mL). Stirring was continued for 1 hour at the same temperature and for 1 hour at room temperature. Water was added, and the organic layer was partitioned, and 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 (130 mg) was obtained. The physical property values are as follows.

Workup

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

Sources & evidence

ORD record
ord-4df4a0576e1944bd84389e93cd05d5ff
Source dataset
uspto-grants-2011_08
Patent number
US08008293B2

Reaction notes

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