tert-butyl N-pyrrolidin-1-ylcarbamate

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

Procedure: 4′-{3-[(3R)-3-Aminopyrrolidinyl]propoxy}[1,1′-biphenyl]-4-carbonitrile and tert-butyl pyrrolidinylcarbamate were processed as described in Examples 9A-9C to provide the title compound.

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

Procedure: 4′-{3-[(3R)-3-Aminopyrrolidinyl]propoxy}[1,1′-biphenyl]-4-carbonitrile and tert-butyl pyrrolidinylcarbamate were processed as described in Examples 9A-9C to provide the title compound.

Conditions: temp:50.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of (3R)-(+)-(tert-butoxycarbonylaminopyrrolidine (1.0 g), p-fluorobenzonitrile (650 mg), cesium carbonate (1.75 g) and 5 ml of DMF was stirred at 50° C. for 12 h. Ethyl acetate and water were then added to the reaction solution, and the organic phase was washed twice with water, dried over sodium sulfate and filtered, and the solvent was removed in vacuo. The residue was purified by preparative HPLC. The product with the molecular weight of 287.36 (C16H21N3O2) was obtained in this way; MS (ESI): 288.20 (M+H+). the organic phase was washed twice with water dried over sodium sulfate filtered the solvent was removed in vacuo The residue was purified by preparative HPLC The product with the molecular weight of 287.36 (C16H21N3O2) was obtained in this way

Conditions: temp:50.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of (3R)-(+)-(tert-butoxycarbonylaminopyrrolidine (1.0 g), p-fluorobenzonitrile (650 mg), cesium carbonate (1.75 g) and 5 ml of DMF was stirred at 50° C. for 12 h. Ethyl acetate and water were then added to the reaction solution, and the organic phase was washed twice with water, dried over sodium sulfate and filtered, and the solvent was removed in vacuo. The residue was purified by preparative HPLC. The product with the molecular weight of 287.36 (C16H21N3O2) was obtained in this way; MS (ESI): 288.20 (M+H+). the organic phase was washed twice with water dried over sodium sulfate filtered the solvent was removed in vacuo The residue was purified by preparative HPLC The product with the molecular weight of 287.36 (C16H21N3O2) was obtained in this way

Conditions: temp:50.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of (3R)-(+)-(tert-butoxycarbonylaminopyrrolidine (1.0 g), p-fluorobenzonitrile (650 mg), cesium carbonate (1.75 g) and 5 ml of DMF was stirred at 50° C. for 12 h. Ethyl acetate and water were then added to the reaction solution, and the organic phase was washed twice with water, dried over sodium sulfate and filtered, and the solvent was removed in vacuo. The residue was purified by preparative HPLC. The product with the molecular weight of 287.36 (C16H21N3O2) was obtained in this way; MS (ESI): 288.20 (M+H+). the organic phase was washed twice with water dried over sodium sulfate filtered the solvent was removed in vacuo The residue was purified by preparative HPLC The product with the molecular weight of 287.36 (C16H21N3O2) was obtained in this way

Conditions: temp:50.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of (3R)-(+)-(tert-butoxycarbonylaminopyrrolidine (1.0 g), p-fluorobenzonitrile (650 mg), cesium carbonate (1.75 g) and 5 ml of DMF was stirred at 50° C. for 12 h. Ethyl acetate and water were then added to the reaction solution, and the organic phase was washed twice with water, dried over sodium sulfate and filtered, and the solvent was removed in vacuo. The residue was purified by preparative HPLC. The product with the molecular weight of 287.36 (C16H21N3O2) was obtained in this way; MS (ESI): 288.20 (M+H+). the organic phase was washed twice with water dried over sodium sulfate filtered the solvent was removed in vacuo The residue was purified by preparative HPLC The product with the molecular weight of 287.36 (C16H21N3O2) was obtained in this way

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

Procedure: 4′-{3-[(3R)-3-Aminopyrrolidinyl]propoxy}[1,1′-biphenyl]-4-carbonitrile and tert-butyl pyrrolidinylcarbamate were processed as described in Examples 9A-9C to provide the title compound.

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

Procedure: 4′-{3-[(3R)-3-Aminopyrrolidinyl]propoxy}[1,1′-biphenyl]-4-carbonitrile and tert-butyl pyrrolidinylcarbamate were processed as described in Examples 9A-9C to provide the title compound.