methyl 2-[1-(aminomethyl)cyclohexyl]acetate

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

Procedure: In an analogous manner as described in Example 2, 1-aminomethyl-1-cyclohexane-acetic acid hydrochloride is reacted with methanol in the presence of hydrogen chloride. After evaporation in a vacuum the residue is recrystallised from methanol/ether to give pure methyl 1-aminomethyl-1-cyclohexane-acetate; m.p. 150° - 152° C. (hydrochloride) After evaporation in a vacuum the residue is recrystallised from methanol/ether

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

Procedure: In an analogous manner as described in Example 2, 1-aminomethyl-1-cyclohexane-acetic acid hydrochloride is reacted with methanol in the presence of hydrogen chloride. After evaporation in a vacuum the residue is recrystallised from methanol/ether to give pure methyl 1-aminomethyl-1-cyclohexane-acetate; m.p. 150° - 152° C. (hydrochloride) After evaporation in a vacuum the residue is recrystallised from methanol/ether

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

Procedure: In an analogous manner as described in Example 2, 1-aminomethyl-1-cyclohexane-acetic acid hydrochloride is reacted with methanol in the presence of hydrogen chloride. After evaporation in a vacuum the residue is recrystallised from methanol/ether to give pure methyl 1-aminomethyl-1-cyclohexane-acetate; m.p. 150° - 152° C. (hydrochloride) After evaporation in a vacuum the residue is recrystallised from methanol/ether

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

Procedure: 1,1-Cyclohexanediacetic acid monomethyl ester is converted via the corresponding acid chloride into the azide. The azide is degraded by the Curtius method to the isocyanate. The isocyanate is then hydrolyzed to give methyl 1-aminomethyl-1-cyclohexaneacetate. Heating this substance in alkaline methanol under reflux for three days affords 8-azaspiro[5,4]decan-9-one or gabapentin lactam.

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

Procedure: 1,1-Cyclohexanediacetic acid monomethyl ester is converted via the corresponding acid chloride into the azide. The azide is degraded by the Curtius method to the isocyanate. The isocyanate is then hydrolyzed to give methyl 1-aminomethyl-1-cyclohexaneacetate. Heating this substance in alkaline methanol under reflux for three days affords 8-azaspiro[5,4]decan-9-one or gabapentin lactam. GBP-L was characterized by means of Thin Layer Chromatography, Infrared-Spectroscopy, [1H]-NMR and [13C]-NMR (Nuclear Magnetic Resonance Spectroscopy) and FAB-MS (Fast Atom Bombardment Mass Spectroscopy).

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

Procedure: In an analogous manner as described in Example 2, 1-aminomethyl-1-cyclohexane-acetic acid hydrochloride is reacted with methanol in the presence of hydrogen chloride. After evaporation in a vacuum the residue is recrystallised from methanol/ether to give pure methyl 1-aminomethyl-1-cyclohexane-acetate; m.p. 150° - 152° C. (hydrochloride) After evaporation in a vacuum the residue is recrystallised from methanol/ether