Water → (4R*,5R*)-5-[(1S*)(5-bromo(2-thienyl))hydroxymethyl]-1-methyl-4-phenylpyrrolidin-2-one

HRID 1837991Notes

Reaction equation

HRID 1837991 reaction equation
[OH:1][C@H:2]([C:16]1[S:17][CH:18]=[CH:19][CH:20]=1)[C@@H:3]1[N:7]([CH3:8])[C:6](=[O:9])[CH2:5][C@@H:4]1[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[Br:21]Br.O>CC(O)=O>[Br:21][C:18]1[S:17][C:16]([C@@H:2]([OH:1])[C@@H:3]2[N:7]([CH3:8])[C:6](=[O:9])[CH2:5][C@@H:4]2[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 962WaterHCID 24408BromineHCID 14071421(+/-)-(4R*,5R*)-5-((1S *)-Hydroxy-2-thienylmethyl)-1-methyl4-phenyl-pyrrolidin-2-one

Product 1

HCID 69891005(4R*,5R*)-5-[(1S*)(5-bromo(2-thienyl))hydroxymethyl]-1-methyl-4-phenylpyrrolidin-2-oneYield 52%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To 0° C. solution of (±)-(4R*,5R*)-5-((1S*)-hydroxy-2-thienylmethyl)-1-methyl-4-phenylpyrrolidin-2-one (9.76 g, 34 mmol) in AcOH (246 mL) was added bromine (2 mL 38.8 mmol). The reaction mixture was allowed to warm to room temperature, stirred for 2 h, then poured into water (500 mL). The resulting mustard colored precipitate was isolated via filtration and washed with water to yield (±)-(4R*,5R*)-5-[(1S*)(5-bromo(2-thienyl))hydroxymethyl]-1-methyl-4-phenylpyrrolidin-2-one (6.47 g, 52%): mp 105° C.; TLC (EtOAc) Rf 0.48.

Workup

  1. customThe resulting mustard colored precipitate was isolated via filtration
  2. washwashed with water

Sources & evidence

ORD record
ord-70295b54fc2e4972a451934249f4abde
Source dataset
uspto-grants-2004_08
Patent number
US06784167B2

Reaction notes

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