Pyridinium hydrobromide → 5-[4-(2-Bromo-2-phenyl-acetyl)-phenyl]-2-oxa-4-aza-bicyclo[3.1.1]heptan-3-one

HRID 872299Notes

Reaction equation

HRID 872299 reaction equation
[C:1]1([CH2:7][C:8]([C:10]2[CH:15]=[CH:14][C:13]([C:16]34[CH2:22][CH:20]([CH2:21]3)[O:19][C:18](=[O:23])[NH:17]4)=[CH:12][CH:11]=2)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[BrH:24].[NH+]1C=CC=CC=1>C1COCC1>[Br:24][CH:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[C:8]([C:10]1[CH:15]=[CH:14][C:13]([C:16]23[CH2:21][CH:20]([CH2:22]2)[O:19][C:18](=[O:23])[NH:17]3)=[CH:12][CH:11]=1)=[O:9]

Participants

4

Reactant 2

HCID 21226041Pyridinium hydrobromideHCID 66665381HCID 66665381, compound

Product 1

HCID 866910395-[4-(2-Bromo-2-phenyl-acetyl)-phenyl]-2-oxa-4-aza-bicyclo[3.1.1]heptan-3-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 5-(4-phenylacetyl-phenyl)-2-oxa-4-aza-bicyclo[3.1.1]heptan-3-one (2.34 g) and pyridinium hydrobromide perbromide (2.22 g) in THF (39 mL) was stirred at rt for 2 hours. The mixture was partitioned between EtOAc and water and the organic phase washed successively with dilute aqueous sodium thiosulfate and brine, dried and concentrated to give the crude title compound which was used in the next step without further purification.

Workup

  1. customThe mixture was partitioned between EtOAc and water
  2. washthe organic phase washed successively with dilute aqueous sodium thiosulfate and brine
  3. customdried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-20769df5b6d649809a15235995dbc015
Source dataset
uspto-grants-2015_03
Patent number
US08975265B2

Reaction notes

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