methyl 2-(cyclohexylamino)acetate

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

Procedure: A solution of cyclohexylamine (34.3 ml) and diazobicycloundecene (DBU, 44.8 ml) in dry tetrahydrofuran (500 ml) under a nitrogen atmosphere was cooled to 0° C. and was treated dropwise with a solution of methyl bromoacetate (28.4 ml) in tetrahydrofuran (50 ml). After stirring at room temperature overnight, the mixture was filtered to remove precipitated DBU-hydrobromide and the solvent evaporated. The resulting residue was dissolved in ether (200 ml), washed with water (2×100 ml), and brine (2×100 ml). The organic extract was dried, filtered and evaporated. Fractional distillation provided 21.1 g., b.p. 160°-170° C. (0.2 mm). the mixture was filtered to remove precipitated DBU-hydrobromide the solvent evaporated The resulting residue was dissolved in ether (200 ml) washed with water (2×100 ml), and brine (2×100 ml) The organic extract was dried filtered evaporated Fractional distillation provided 21.1 g

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

Procedure: A solution of cyclohexylamine (34.3 ml) and diazobicycloundecene (DBU, 44.8 ml) in dry tetrahydrofuran (500 ml) under a nitrogen atmosphere was cooled to 0° C. and was treated dropwise with a solution of methyl bromoacetate (28.4 ml) in tetrahydrofuran (50 ml). After stirring at room temperature overnight, the mixture was filtered to remove precipitated DBU-hydrobromide and the solvent evaporated. The resulting residue was dissolved in ether (200 ml), washed with water (2×100 ml), and brine (2×100 ml). The organic extract was dried, filtered and evaporated. Fractional distillation provided 21.1 g., b.p. 160°-170° C. (0.2 mm). the mixture was filtered to remove precipitated DBU-hydrobromide the solvent evaporated The resulting residue was dissolved in ether (200 ml) washed with water (2×100 ml), and brine (2×100 ml) The organic extract was dried filtered evaporated Fractional distillation provided 21.1 g