methyl 2-oxobicyclo[3.1.0]hexane-1-carboxylate

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In argon atmosphere, potassium cyanide (260 mg, 4 mmol) and 2-oxo-bicyclo [3.1.0] hexane-1-carboxylic acid methyl ester (462 mg, 3 mmol) were added to dimethylformamide (3 ml). The mixture was stirred at the room temperature for 24 hours and was treated in accordance with the process of Preparation 4 to obtain 290 mg of 5-cyanomethyl-2-oxo-cyclopentanecarboxylic acid methyl ester. Yield: 53%. was treated in accordance with the process of Preparation 4

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In argon atmosphere, potassium cyanide (260 mg, 4 mmol) and 2-oxo-bicyclo [3.1.0] hexane-1-carboxylic acid methyl ester (462 mg, 3 mmol) were added to hexamethylphosphoric triamide (3 ml). The mixture was stirred at the room temperature for 24 hours and was treated in accordance with the process of Preparation 4 to obtain 300 mg of 5-cyanomethyl-2-oxo-cyclopentanecarboxylic acid methyl ester. Yield: 55%. was treated in accordance with the process of Preparation 4

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In argon atmosphere, potassium cyanide (260 mg, 4 mmol) and 2-oxo-bicyclo [3.1.0] hexane-1-carboxylic acid methyl ester (462 mg, 3 mmol) were added to hexamethylphosphoric triamide (3 ml). The mixture was stirred at the room temperature for 24 hours and was treated in accordance with the process of Preparation 4 to obtain 300 mg of 5-cyanomethyl-2-oxo-cyclopentanecarboxylic acid methyl ester. Yield: 55%. was treated in accordance with the process of Preparation 4

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In argon atmosphere, sodium cyanide (200 mg, 4 mmol) and 2-oxo-bicyclo [3.1.0] hexane-1-carboxylic acid methyl ester (462 mg, 3 mmol) were added to dimethyl sulfoxide (2ml). The mixture was stirred at the room temperature for one night and was treated in accordance with the process of Preparation 4 to obtain 328 mg of 5-cyanomethyl-2-oxo-cyclopentanecarboxylic acid methyl ester. Yield: 60%. was treated in accordance with the process of Preparation 4

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In argon atmosphere, 2-diazo-3-oxo-6-heptenoic acid methyl ester (34 g, 0.187 mmol) was dissolved in benzene (300 ml). An acetyl acetone-copper complex (1 g) was added to the solution. The mixture was stirred for one night under refluxing. After cooling it, the solvent was distilled off under a reduced pressure. The residue was purified by a distillation to obtain 17.1 g of 2-oxo-bicyclo [3.1.0] hexane-1-carboxylic acid methyl ester. Yield: 60%. Boiling point: 83° to 85° C/0.3 mmHg. An acetyl acetone-copper complex (1 g) was added to the solution under refluxing After cooling it the solvent was distilled off under a reduced pressure The residue was purified by a distillation

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In argon atmosphere, 2-diazo-3-oxo-6-heptenoic acid methyl ester (34 g, 0.187 mmol) was dissolved in benzene (300 ml). An acetyl acetone-copper complex (1 g) was added to the solution. The mixture was stirred for one night under refluxing. After cooling it, the solvent was distilled off under a reduced pressure. The residue was purified by a distillation to obtain 17.1 g of 2-oxo-bicyclo [3.1.0] hexane-1-carboxylic acid methyl ester. Yield: 60%. Boiling point: 83° to 85° C/0.3 mmHg. An acetyl acetone-copper complex (1 g) was added to the solution under refluxing After cooling it the solvent was distilled off under a reduced pressure The residue was purified by a distillation