4-(3-aminopropyl)phenol

Conditions: temp:0.00; pressure:0.00; stir:

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

Procedure: 100% Palladium-carbon catalyst (water content 50%, 120 mg) was added to a solution of 3-(4-benzyloxyphenyl)propylamine (620 mg, 2.57 mmol, 1.0 eq) in THF (10 ml), and the mixture was stirred for 2 hours at room temperature in a stream of hydrogen. The reaction mixture was filtered through Celite, and the filtrate was concentrated under reduced pressure to give 3-(4-hydroxyphenyl)propylamine (354 mg, 91.1%). The reaction mixture was filtered through Celite the filtrate was concentrated under reduced pressure

Conditions: temp:0.00; pressure:0.00; stir:

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

Procedure: To a solution of tert-butyl N-{3-hydroxy-2-[4-(3-phenylpropoxy)benzyl]propyl}-β-alaninate (65 mg; prepared by following the procedure of Example 4 using the compound prepared in Example 15 as a substitute for 4-(3-aminopropyl)phenol) in dichloromethane (3 mL), trifluoroacetic acid (3 mL) was dropped at 0° C., followed by stirring at room temperature for 2 hours. Then, the reaction mixture was concentrated. The residue was purified by silica gel column chromatography (chloroform:methanol:aqueous ammonia=80:20:4). The crude product thus obtained was washed with diethyl ether to give the title compound (38 mg) having the following physical properties. prepared Then, the reaction mixture was concentrated The residue was purified by silica gel column chromatography (chloroform:methanol:aqueous ammonia=80:20:4) The crude product thus obtained was washed with diethyl ether

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

Procedure: To a methanol solution (25 mL) of 4-(3-aminopropyl)phenol (1.83 g), tert-butyl acrylate (1.7 mL) was added dropwise thereto at room temperature, followed by stirring at room temperature overnight. The reaction mixture was concentrated. The residue was purified by silica gel column chromatography (ethyl acetate→ethyl acetate:methanol=3:1) to give the title compound (1.55 g) having the following physical properties. at room temperature The reaction mixture was concentrated The residue was purified by silica gel column chromatography (ethyl acetate→ethyl acetate:methanol=3:1)

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

Procedure: To a solution of tert-butyl N-{3-hydroxy-2-[4-(3-phenylpropoxy)benzyl]propyl}-β-alaninate (65 mg; prepared by following the procedure of Example 4 using the compound prepared in Example 15 as a substitute for 4-(3-aminopropyl)phenol) in dichloromethane (3 mL), trifluoroacetic acid (3 mL) was dropped at 0° C., followed by stirring at room temperature for 2 hours. Then, the reaction mixture was concentrated. The residue was purified by silica gel column chromatography (chloroform:methanol:aqueous ammonia=80:20:4). The crude product thus obtained was washed with diethyl ether to give the title compound (38 mg) having the following physical properties. prepared Then, the reaction mixture was concentrated The residue was purified by silica gel column chromatography (chloroform:methanol:aqueous ammonia=80:20:4) The crude product thus obtained was washed with diethyl ether

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

Procedure: To a methanol solution (25 mL) of 4-(3-aminopropyl)phenol (1.83 g), tert-butyl acrylate (1.7 mL) was added dropwise thereto at room temperature, followed by stirring at room temperature overnight. The reaction mixture was concentrated. The residue was purified by silica gel column chromatography (ethyl acetate→ethyl acetate:methanol=3:1) to give the title compound (1.55 g) having the following physical properties. TLC: Rf 0.24 (ethyl acetate:methanol 5:1); at room temperature The reaction mixture was concentrated The residue was purified by silica gel column chromatography (ethyl acetate→ethyl acetate:methanol=3:1)

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

Procedure: 100% Palladium-carbon catalyst (water content 50%, 120 mg) was added to a solution of 3-(4-benzyloxyphenyl)propylamine (620 mg, 2.57 mmol, 1.0 eq) in THF (10 ml), and the mixture was stirred for 2 hours at room temperature in a stream of hydrogen. The reaction mixture was filtered through Celite, and the filtrate was concentrated under reduced pressure to give 3-(4-hydroxyphenyl)propylamine (354 mg, 91.1%). The reaction mixture was filtered through Celite the filtrate was concentrated under reduced pressure