Triethylamine → tert-Butyl (3-benzyl-3-azabicyclo[3.1.0]hexan-6-yl)carbamate

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Reaction Steps

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%).

Provenance & Evidence