Sodium Bicarbonate → HCID 87983157, compound

HRID 1359351Notes

Reaction equation

HRID 1359351 reaction equation
O.C1(C)C=CC(S(O)(=O)=O)=CC=1.[Br:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([N:20]2[CH2:24][C@@H:23]([O:25][CH2:26][CH2:27][O:28]C3CCCCO3)[C@H:22]([O:35][CH2:36][O:37][CH3:38])[CH2:21]2)[N:15]=1.C(=O)(O)[O-].[Na+]>O.C1(C)C=CC(S(O)(=O)=O)=CC=1.CO>[Br:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([N:20]2[CH2:24][C@@H:23]([O:25][CH2:26][CH2:27][OH:28])[C@H:22]([O:35][CH2:36][O:37][CH3:38])[CH2:21]2)[N:15]=1

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 521998p-Toluenesulfonic acid monohydrateHCID 87983301HCID 87983301, compound

Product 1

HCID 87983157HCID 87983157, compound

Reagents, catalysts & solvents 2

HCID 521998p-Toluenesulfonic acid monohydrateCatalystHCID 887MethanolSolvent

Procedure

2.26 g p-toluenesulfonic acid monohydrate was added dropwise little by little into a solution of 60 ml of methanol containing 17.09 g of 2-bromo-6-[(3R,4R)-3-methoxymethyloxy-4-[2-(tetrahydro-2H-2-pyranyloxy)ethyl]oxypyrrolidine-1-yl]pyridine in an ice bath. After stirring for 30 minutes under ice-cooling, it was stirred at room temperature for 2 hours. 377 mg of p-toluenesulfonic acid monohydrate was further added thereto, followed by stirring for 2 hours. Then, the reaction solution was poured into aqueous saturated sodium bicarbonate and extracted twice with ethyl acetate. The organic phase was washed with brine and the solvent was removed. The residue was filtered through silica gel, to give 13.14 g of the target compound.

Workup

  1. temperaturecooling
  2. stirringit was stirred at room temperature for 2 hours
  3. stirringby stirring for 2 hours
  4. extractionextracted twice with ethyl acetate
  5. washThe organic phase was washed with brine
  6. customthe solvent was removed
  7. filtrationThe residue was filtered through silica gel

Sources & evidence

ORD record
ord-5877aa6a3f354c15a83e630acd7056ab
Source dataset
uspto-grants-2003_07
Patent number
US06599917B1

Reaction notes

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