Water → (RS)-1-(4-benzyloxy-phenyl)-3-bromo-pyrrolidin-2-one

HRID 1768127Notes

Reaction equation

HRID 1768127 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([NH:15][C:16](=[O:22])[CH:17]([Br:21])[CH2:18][CH2:19]Br)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].O>ClCCl>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([N:15]2[CH2:19][CH2:18][CH:17]([Br:21])[C:16]2=[O:22])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 23614762(RS)-N-(4-Benzyloxy-phenyl)-2,4-dibromo-butyramide

Product 1

HCID 23614761(RS)-1-(4-benzyloxy-phenyl)-3-bromo-pyrrolidin-2-oneYield 35%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

6.1 g (14.3 mmol) (RS)—N-(4-benzyloxy-phenyl)-2,4-dibromo-butyramide and 0.1 g of Dowex 2×10 are suspended in 50 ml dichloromethane. 7 ml of a 50% aqueous sodium hydroxide solution is slowly added under vigorous stirring. The resulting reaction mixture is stirred overnight at RT, then poured into 25 ml of cold water. The organic phase is separated, dried and evaporated. The crude material is recrystallised from ethyl acetate to yield 1.72 g (35%) of a brownish solid. Mp=125–126° C.

Workup

  1. customThe resulting reaction mixture
  2. customThe organic phase is separated
  3. customdried
  4. customevaporated
  5. customThe crude material is recrystallised from ethyl acetate

Sources & evidence

ORD record
ord-89e12858f1074c73be43b82f1e571513
Source dataset
uspto-grants-2007_06
Patent number
US07235581B2

Reaction notes

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