Sulfoxonium, trimethyl-, iodide (1:1) → Benzyl 8-azaspiro[bicyclo[3.2.1]octane-3,2'-oxirane]-8-carboxylate

HRID 588702Notes

Reaction equation

HRID 588702 reaction equation
[CH3:1][C:2]([CH3:5])([O-:4])[CH3:3].[K+].[I-].C[S+](C)(C)=O.O=C1C[CH:19]2[N:21]([C:22]([O:24][CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[O:23])[CH:16]([CH2:17][CH2:18]2)C1>O1CCCC1.C1(C)C=CC=CC=1.O>[O:4]1[CH2:1][C:2]21[CH2:5][CH:19]1[N:21]([C:22]([O:24][CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[O:23])[CH:16]([CH2:17][CH2:18]1)[CH2:3]2

Participants

7

Reactant 3

HCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 146825353-Oxo-8-aza-bicyclo[3.2.1]octane-8-carboxylic acid benzyl esterHCID 23665647Potassium tert-butoxide

Product 1

HCID 74394144Benzyl 8-azaspiro[bicyclo[3.2.1]octane-3,2'-oxirane]-8-carboxylate

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a 500-mL, three-necked, round-bottomed flask equipped with a magnetic stirring bar, a thermometer, and a condenser was charged tetrahydrofuran (163 mL), potassium tert-butoxide (6.6 g, 95% pure) and trimethylsulfoxonium iodide (13.0 g). The mixture was heated to reflux and stirred for 3 hours. A solution of benzyl 3-oxo-8-azabicyclo[3.2.1]octane-8-carboxylate (10.0 g) in tetrahydrofuran (37 mL) was added in one portion. The reaction mixture was refluxed for another 2 hours. The mixture was cooled to room temperature and diluted with toluene (100 mL) and water. The water layer was separated and extracted with toluene (2×50 mL). The combined organic layers were washed with water (3×40 mL) and concentrated under vacuum to provide the title compound.

Workup

  1. customTo a 500-mL, three-necked, round-bottomed flask equipped with a magnetic stirring bar
  2. temperatureThe mixture was heated
  3. temperatureto reflux
  4. temperatureThe reaction mixture was refluxed for another 2 hours
  5. customThe water layer was separated
  6. extractionextracted with toluene (2×50 mL)
  7. washThe combined organic layers were washed with water (3×40 mL)
  8. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-c157054e46074500a0f7243282a06da7
Source dataset
uspto-grants-2016_01
Patent number
US09227963B2

Reaction notes

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