Dimethylformamide → HCID 87982988, compound

HRID 1359353Notes

Reaction equation

HRID 1359353 reaction equation
[H-].[Na+].CN(C)C=O.[Br:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([N:15]2[CH2:19][C@@H:18]([O:20][CH2:21][CH2:22]OS(C)(=O)=O)[C@H:17]([OH:28])[CH2:16]2)[N:10]=1>O>[Br:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([N:15]2[CH2:16][C@H:17]3[O:28][CH2:22][CH2:21][O:20][C@@H:18]3[CH2:19]2)[N:10]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 24758Sodium hydride2×HCID 87983249HCID 87983249, compound

Product 1

HCID 87982988HCID 87982988, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1.49 g of 60% oily sodium hydride was added little by little to a solution of 150 ml of N,N-dimethylformamide containing 11.82 g of 2-bromo-6-[(3R,4R)-3-hydroxy-4-(2-methanesulfonyloxyethyl)oxypyrrolidine-1-yl]pyridine under stirring in an ice bath. Then, after stirring at room temperature for one hour, 372 mg of 60% oily sodium hydride was added thereto. After stirred for further 45 minutes, the reaction mixture was poured into water and extracted twice with ethyl acetate. The organic phase was washed with water and brine, and the solvent was removed. The residue was crystallized from ethyl acetate/hexane, to give 5.35 g of the target compound.

Workup

  1. stirringThen, after stirring at room temperature for one hour
  2. stirringAfter stirred for further 45 minutes
  3. extractionextracted twice with ethyl acetate
  4. washThe organic phase was washed with water and brine
  5. customthe solvent was removed
  6. customThe residue was crystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-47e47aede5e844239939b35beb17eb74
Source dataset
uspto-grants-2003_07
Patent number
US06599917B1

Reaction notes

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