Bis-(1H-imidazol-2-YL)-methanone → (4R)-5,5-Dimethyl-4-phenyl-1,3-oxazolidin-2-one

HRID 2392834Notes

Reaction equation

HRID 2392834 reaction equation
[NH2:1][C@H:2]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[C:3]([CH3:6])([OH:5])[CH3:4].[C:13](C1NC=CN=1)(C1NC=CN=1)=[O:14]>ClCCl>[C:7]1([C@@H:2]2[C:3]([CH3:6])([CH3:4])[O:5][C:13](=[O:14])[NH:1]2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

4

Reactant 2

HCID 5250894Bis-(1H-imidazol-2-YL)-methanoneHCID 11240681(βR)-β-Amino-α,α-dimethylbenzeneethanol

Product 1

HCID 6950851(4R)-5,5-Dimethyl-4-phenyl-1,3-oxazolidin-2-oneYield 82.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (13) (1.30 g, 7.89 mmol) in dichloromethane (100 ml) was added carbonyl diimidazole (1.534 g, 9.47 mmol) and the reaction mixture was refluxed for 2 hours. The reaction was quenched with hydrochloric acid (1M) and the product extracted repeatedly with dichloromethane. The combined organic extracts were dried over magnesium sulphate. After concentration in vacuo the residue was purified by flash column chromatography using 40% ethyl acetate/40-60 petroleum ether as eluant to give the title compound (15) (1.24 g, 82%).

Workup

  1. temperaturethe reaction mixture was refluxed for 2 hours
  2. customThe reaction was quenched with hydrochloric acid (1M)
  3. extractionthe product extracted repeatedly with dichloromethane
  4. dry with materialThe combined organic extracts were dried over magnesium sulphate
  5. concentrationAfter concentration in vacuo the residue
  6. customwas purified by flash column chromatography

Sources & evidence

ORD record
ord-2b20d07d42ed4c48b8d5920618b96d1c
Source dataset
uspto-grants-1998_09
Patent number
US05801249

Reaction notes

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