Dichloromethane → HCID 87983204, compound

HRID 1359352Notes

Reaction equation

HRID 1359352 reaction equation
C(N(CC)CC)C.ClCCl.[Br:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([N:18]2[CH2:22][C@@H:21]([O:23][CH2:24][CH2:25][OH:26])[C@H:20]([O:27][CH2:28][O:29][CH3:30])[CH2:19]2)[N:13]=1.[CH3:31][S:32](Cl)(=[O:34])=[O:33]>O>[Br:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([N:18]2[CH2:22][C@@H:21]([O:23][CH2:24][CH2:25][O:26][S:32]([CH3:31])(=[O:34])=[O:33])[C@H:20]([O:27][CH2:28][O:29][CH3:30])[CH2:19]2)[N:13]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 87983157HCID 87983157, compound

Product 1

HCID 87983204HCID 87983204, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

7.9 ml of triethylamine was slowly added to a solution of 70 ml of dichloromethane containing 13.14 g of 2-bromo-6-[(3R,4R)-3-methoxymethyloxy-4-(2-hydroxyethyl)oxypyrrolidine-1-yl]pyridine in an ice bath. Then, 3.2 ml of methanesulfonyl chloride was slowly added thereto, followed by stirring for 15 minutes. Then, the reaction solution was poured into water and extracted twice with dichloromethane. The organic phase was washed with brine and the solvent was removed. The residue was filtered through NH-silica gel, to give 15.66 g of the target compound.

Workup

  1. extractionextracted twice with dichloromethane
  2. washThe organic phase was washed with brine
  3. customthe solvent was removed
  4. filtrationThe residue was filtered through NH-silica gel

Sources & evidence

ORD record
ord-d3c9de98f9c34d1f9d6781d13a8c9193
Source dataset
uspto-grants-2003_07
Patent number
US06599917B1

Reaction notes

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