Water → 2-Phenyl-3-(toluene-4-sulfonyl)-3-aza-bicyclo[3.1.0]hexane-1-carboxylic acid ethyl ester

HRID 1295346Notes

Reaction equation

HRID 1295346 reaction equation
COC([C:5]1[CH:6]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[N:7]([S:10]([C:13]2[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=2)(=[O:12])=[O:11])[CH2:8][CH:9]=1)=O.[I-].C[S+](C)(C)=[O:29].[H-].[Na+].O.[CH2:35]1[CH2:39][O:38][CH2:37][CH2:36]1>CS(C)=O>[CH2:39]([O:38][C:37]([C:36]12[CH2:5][CH:9]1[CH2:8][N:7]([S:10]([C:13]1[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=1)(=[O:12])=[O:11])[CH:6]2[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)=[O:29])[CH3:35]

Participants

7

Reactant 5

HCID 962WaterHCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 15306355Dwkzwchktszxga-uhfffaoysa-

Product 1

HCID 589073302-Phenyl-3-(toluene-4-sulfonyl)-3-aza-bicyclo[3.1.0]hexane-1-carboxylic acid ethyl esterYield 58.8%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
-20 °C

Procedure

Racemic 2-phenyl-1-(toluene-4-sulfonyl)-2,5-dihydro-1H-pyrrole-3-carboxylic acid methyl ester (JOC 1998, 63, 5031-5041), (10.2 g, 27.5 mmol) and trimethylsulfoxoniumiodide (Aldrich), (6.6 9, 30.2 mmol) were dissolved in DMSO (100 mL), diluted with THF (200 mL), and cooled to −20° C. Oil free sodium hydride (0.8 g, 33.0 mmol) was added portionwise over approximately 20 minutes, the reaction was allowed to warm to room temperature and stirred 16 hours. The reaction mixture was poured into approximately 500 mL cold water and extracted with EtOAc. The EtOAc was washed with water two times and the aqueous extracts were combined and extracted with EtOAc. The last EtOAc extract was washed with water two times and the organic extracts were combined and washed with brine, dried over magnesium sulfate, and concentrated to a yellow gum. The gum was diluted with 45-50 mL Et2O and cooled. Scratching induced crystallization and the resultant crystals were collected by filtration to yield 2-phenyl-3-(toluene-4-sulfonyl)-3-aza-bicyclo[3.1.0]hexane-1-carboxylic acid ethyl ester (6.23 g, 58.8% yield).

Workup

  1. temperatureto warm to room temperature
  2. extractionextracted with EtOAc
  3. washThe EtOAc was washed with water two times
  4. extractionextracted with EtOAc
  5. extractionThe last EtOAc extract
  6. washwas washed with water two times
  7. washwashed with brine
  8. dry with materialdried over magnesium sulfate
  9. concentrationconcentrated to a yellow gum
  10. additionThe gum was diluted with 45-50 mL Et2O
  11. temperaturecooled
  12. customcrystallization
  13. filtrationthe resultant crystals were collected by filtration

Sources & evidence

ORD record
ord-107b55b0a8d041b9bf694049aeadd2a9
Source dataset
uspto-grants-2007_07
Patent number
US07241798B2

Reaction notes

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