4-(phenylmethoxycarbonylamino)butyl methanesulfonate

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

Procedure: To a solution of N-(benzyloxycarbonyl)-4-(mesyloxy)butylamine (2.51 g) in anhydrous dimethylformamide (28 ml) are added 2.0 M dimethylamine THF solution 12.5 ml. anhydrous potassium carbonate (1.72 g) and sodium iodide (3.74 g), and the mixture is stirred at room temperature overnight. Water is added to the reaction mixture, and the whole is extracted with ether. The organic layer is washed with water and saturated brine successively, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The resulting residue is purified by silica gel column chromatography to give 1.59 g (76%) of N-(benzyloxycarbonyl)-4-(dimethylamino)butylamine. the whole is extracted with ether The organic layer is washed with water and saturated brine successively dried over anhydrous magnesium sulfate concentrated under reduced pressure The resulting residue is purified by silica gel column chromatography

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

Procedure: To a solution of N-(benzyloxycarbonyl)-4-(mesyloxy)butylamine (2.51 g) in anhydrous dimethylformamide (28 ml) are added 2.0 M dimethylamine THF solution 12.5 ml. anhydrous potassium carbonate (1.72 g) and sodium iodide (3.74 g), and the mixture is stirred at room temperature overnight. Water is added to the reaction mixture, and the whole is extracted with ether. The organic layer is washed with water and saturated brine successively, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The resulting residue is purified by silica gel column chromatography to give 1.59 g (76%) of N-(benzyloxycarbonyl)-4-(dimethylamino)butylamine. the whole is extracted with ether The organic layer is washed with water and saturated brine successively dried over anhydrous magnesium sulfate concentrated under reduced pressure The resulting residue is purified by silica gel column chromatography

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

Procedure: To a solution of N-(benzyloxycarbonyl)-4-(mesyloxy)butylamine (2.51 g) in anhydrous dimethylformamide (28 ml) are added dimethylamine (12.5 ml), anhydrous potassium carbonate (1.72 g) and sodium iodide (3.74 g), and the mixture is stirred at room temperature overnight. Water is added to the reaction mixture, and the whole is extracted with ether. The organic layer is washed with water and saturated brine successively, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The resulting residue is purified by silica gel column chromatography to give 1.59 g (76%) of N-(benzyloxycarbonyl)-4-(dimethylamino)butylamine. the whole is extracted with ether The organic layer is washed with water and saturated brine successively dried over anhydrous magnesium sulfate concentrated under reduced pressure The resulting residue is purified by silica gel column chromatography

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

Procedure: Following the general procedure of Example 4, Step 2, and making non-critical variations but using 4-(benzyloxycarbonylamino)butyl methanesulfonate and commercially available N-ethylcyclopropanamine, benzyl 4-(cyclopropyl(ethyl)amino)butylcarbamate was obtained.

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

Procedure: Following the general procedure of Example 4, Step 2, and making non-critical variations but using 4-(benzyloxycarbonylamino)butyl methanesulfonate and ethyl amine in THF, the compound of Step 1 was obtained.

Conditions: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a pressure vessel was added 4-(benzyloxycarbonylamino)butyl methanesulfonate (330 mg, 1.10 mmol) and pyrrolidine (234 mg, 3.3 mmol) in THF. The reaction was heated to 100° C., stirred overnight, cooled to 20-25° C., and concentrated. The crude concentrate was purified by Biotage column chromatography to give benzyl 4-(pyrrolidin-1-yl)butylcarbamate (200 mg). cooled to 20-25° C. concentrated The crude concentrate was purified by Biotage column chromatography

Conditions: temp:22.51; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of benzyl 4-hydroxybutylcarbamate (1.1 g, 4.9 mmol) and triethylamine (1.7 mL, 9.8 mmol) in THF was added methanesulfonyl chloride (0.67 g, 5.9 mmol) at 0° C. The reaction was stirred at 20-25° C. for 6 hours and concentrated. The residue was partitioned between ethyl acetate and water. The phases were separated, and the organic layer was washed with hydrochloride solution (1 N), saturated sodium bicarbonate solution, and saline. The separated organic layer was dried and concentrated to give 4-(benzyloxycarbonylamino)butyl methanesulfonate (1.2 g). concentrated The residue was partitioned between ethyl acetate and water The phases were separated the organic layer was washed with hydrochloride solution (1 N), saturated sodium bicarbonate solution, and saline The separated organic layer was dried concentrated