tert-butyl N-(3-benzyl-3-azabicyclo[3.1.0]hexan-6-yl)carbamate

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

Procedure: A mixture of 3-benzyl-3-azabicyclo[3.1.0]hexane-6-carboxylic acid (116 mg, 0.53 mmol) obtained by treating ethyl 3-benzyl-3-azabicyclo[3.1.0]hexane-6-carboxylate obtained in step 5 of Example 1, with an aqueous solution of NaOH, with triethylamine (239 mg, 2.36 mmol), DPPA (303 mg, 1.10 mmol) and t-butanol (4 ml), was heated under reflux in a nitrogen atmosphere for 19 hours, followed by cooling the reaction mixture, pouring it into water, extracting with toluene, washing the organic layer successively with an aqueous solution of Na2CO3, water and a saturated aqueous solution of NaCl, drying over anhydrous magnesium sulfate, distilling off the solvent under reduced pressure and purifying the residue according to thin-layer chromatography (developing solvent: chloroform:methanol=20:1), to obtain 3-benzyl-6-t-butoxycarbonylamino-3-azabicyclo[3.1.0]hexane (47 mg, 0.16 mmol, 31%). obtained under reflux in a nitrogen atmosphere for 19 hours by cooling the reaction mixture extracting with toluene washing the organic layer successively with an aqueous solution of Na2CO3, water a saturated aqueous solution of NaCl, drying over anhydrous magnesium sulfate distilling off the solvent under reduced pressure purifying the residue

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

Procedure: A mixture of 3-benzyl-3-azabicyclo[3.1.0]hexane-6-carboxylic acid hydrochloride (101 mg, 0.40 mmol), triethylamine (185 mg, 1.83 mmol), DPPA (180 mg, 0.65 mmol), t-butanol (4 ml) and toluene (3 ml) was heated under reflux in a nitrogen atmosphere for 23 hours, followed by cooling the reaction mixture, pouring it into water, extracting with toluene, washing the organic layer successively with an aqueous solution of sodium carbonate, water and a saturated aqueous NaCl solution, drying over anhydrous magnesium sulfate, distilling off the solvent under reduced pressure, and purifying the residue according to thin-layer chromatography (developing solvent: chloroform:methanol=20:1), to obtain 3-benzyl-6-t-butoxycarbonylamino-3-azabicyclo[3.1.0]hexane (27 mg, 0.09 mmol, 24%). was heated under reflux in a nitrogen atmosphere for 23 hours by cooling the reaction mixture extracting with toluene washing the organic layer successively with an aqueous solution of sodium carbonate, water a saturated aqueous NaCl solution, drying over anhydrous magnesium sulfate distilling off the solvent under reduced pressure purifying the residue

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

Procedure: A mixture of 3-benzyl-3-azabicyclo[3.1.0]hexane-6-carboxylic acid (116 mg, 0.53 mmol) obtained by treating ethyl 3-benzyl-3-azabicyclo[3.1.0]hexane-6-carboxylate obtained in step 5 of Example 1, with an aqueous solution of NaOH, with triethylamine (239 mg, 2.36 mmol), DPPA (303 mg, 1.10 mmol) and t-butanol (4 ml), was heated under reflux in a nitrogen atmosphere for 19 hours, followed by cooling the reaction mixture, pouring it into water, extracting with toluene, washing the organic layer successively with an aqueous solution of Na2CO3, water and a saturated aqueous solution of NaCl, drying over anhydrous magnesium sulfate, distilling off the solvent under reduced pressure and purifying the residue according to thin-layer chromatography (developing solvent: chloroform:methanol=20:1), to obtain 3-benzyl-6-t-butoxycarbonylamino-3-azabicyclo[3.1.0]hexane (47 mg, 0.16 mmol, 31%). obtained under reflux in a nitrogen atmosphere for 19 hours by cooling the reaction mixture extracting with toluene washing the organic layer successively with an aqueous solution of Na2CO3, water a saturated aqueous solution of NaCl, drying over anhydrous magnesium sulfate distilling off the solvent under reduced pressure purifying the residue

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

Procedure: A mixture of 3-benzyl-3-azabicyclo[3.1.0]hexane-6-carboxylic acid hydrochloride (101 mg, 0.40 mmol), triethylamine (185 mg, 1.83 mmol), DPPA (180 mg, 0.65 mmol), t-butanol (4 ml) and toluene (3 ml) was heated under reflux in a nitrogen atmosphere for 23 hours, followed by cooling the reaction mixture, pouring it into water, extracting with toluene, washing the organic layer successively with an aqueous solution of sodium carbonate, water and a saturated aqueous NaCl solution, drying over anhydrous magnesium sulfate, distilling off the solvent under reduced pressure, and purifying the residue according to thin-layer chromatography (developing solvent: chloroform:methanol=20:1), to obtain 3-benzyl-6-t-butoxycarbonylamino-3-azabicyclo[3.1.0]hexane (27 mg, 0.09 mmol, 24%). was heated under reflux in a nitrogen atmosphere for 23 hours by cooling the reaction mixture extracting with toluene washing the organic layer successively with an aqueous solution of sodium carbonate, water a saturated aqueous NaCl solution, drying over anhydrous magnesium sulfate distilling off the solvent under reduced pressure purifying the residue

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

Procedure: A mixture of 3-benzyl-3-azabicyclo[3.1.0]hexane-6-carboxylic acid (116 mg, 0.53 mmol) obtained by treating ethyl 3-benzyl-3-azabicyclo[3.1.0]hexane-6-carboxylate obtained in step 5 of Example 1, with an aqueous solution of NaOH, with triethylamine (239 mg, 2.36 mmol), DPPA (303 mg, 1.10 mmol) and t-butanol (4 ml), was heated under reflux in a nitrogen atmosphere for 19 hours, followed by cooling the reaction mixture, pouring it into water, extracting with toluene, washing the organic layer successively with an aqueous solution of Na2CO3, water and a saturated aqueous solution of NaCl, drying over anhydrous magnesium sulfate, distilling off the solvent under reduced pressure and purifying the residue according to thin-layer chromatography (developing solvent: chloroform:methanol=20:1), to obtain 3-benzyl-6-t-butoxycarbonylamino-3-azabicyclo[3.1.0]hexane (47 mg, 0.16 mmol, 31%). obtained under reflux in a nitrogen atmosphere for 19 hours by cooling the reaction mixture extracting with toluene washing the organic layer successively with an aqueous solution of Na2CO3, water a saturated aqueous solution of NaCl, drying over anhydrous magnesium sulfate distilling off the solvent under reduced pressure purifying the residue

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

Procedure: A mixture of 3-benzyl-3-azabicyclo[3.1.0]hexane-6-carboxylic acid hydrochloride (101 mg, 0.40 mmol), triethylamine (185 mg, 1.83 mmol), DPPA (180 mg, 0.65 mmol), t-butanol (4 ml) and toluene (3 ml) was heated under reflux in a nitrogen atmosphere for 23 hours, followed by cooling the reaction mixture, pouring it into water, extracting with toluene, washing the organic layer successively with an aqueous solution of sodium carbonate, water and a saturated aqueous NaCl solution, drying over anhydrous magnesium sulfate, distilling off the solvent under reduced pressure, and purifying the residue according to thin-layer chromatography (developing solvent: chloroform:methanol=20:1), to obtain 3-benzyl-6-t-butoxycarbonylamino-3-azabicyclo[3.1.0]hexane (27 mg, 0.09 mmol, 24%). was heated under reflux in a nitrogen atmosphere for 23 hours by cooling the reaction mixture extracting with toluene washing the organic layer successively with an aqueous solution of sodium carbonate, water a saturated aqueous NaCl solution, drying over anhydrous magnesium sulfate distilling off the solvent under reduced pressure purifying the residue