Ethylene Glycol → trans-1-Benzoyl-3-bromo-4-(2-hydroxyethoxy)-pyrrolidine

HRID 1648477

Reaction equation

HRID 1648477 reaction equation
[C:1]([N:9]1[CH2:13][CH:12]=[CH:11][CH2:10]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br:14]N1C(=O)CCC1=O.O.[CH2:23]([OH:26])[CH2:24][OH:25]>>[C:1]([N:9]1[CH2:13][C@@H:12]([O:25][CH2:24][CH2:23][OH:26])[C@H:11]([Br:14])[CH2:10]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 4

HCID 174Ethylene GlycolHCID 962WaterHCID 67184N-bromobutanimideHCID 112522831H-Pyrrole, 1-benzoyl-2,5-dihydro-

Product 1

HCID 67598706trans-1-Benzoyl-3-bromo-4-(2-hydroxyethoxy)-pyrrolidine

Procedure

95 g (0.55 mol) of 1-benzoyl-3-pyrroline are dissolved in 380 g of ethylene glycol, and 101 g (0.57 mol) of N-bromosuccinimide are added in 5 g portions over a period of 2 hours at room temperature. The mixture is then stirred overnight at room temperature and poured into water, followed by extraction with methylene chloride, drying over magnesium sulphate and concentration of the solution. The residue (188 g) was chromatographed with ethyl acetate on silica gel.

Workup

  1. extractionfollowed by extraction with methylene chloride
  2. dry with materialdrying over magnesium sulphate and concentration of the solution
  3. customThe residue (188 g) was chromatographed with ethyl acetate on silica gel

Sources & evidence

ORD record
ord-099060e53aa9435c9af0c2e09017c8a9
Source dataset
uspto-grants-1995_07
Patent number
US05436334

Linked notes

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