3-amino-2-phenylpropan-1-ol

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

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

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

Procedure: For the preparation of the alcohols VI used in Examples (3a) and (3b). 10 g of 3-amino-2-phenylpropanecarboxylic acid in 150 ml of monoglyme were stirred with 3 g of LiAlH4 for 20 hrs. Then, 12 ml of water and 3 ml of 10% sodium hydroxide solution were slowly added thereto. The mixture was filtered and the filtrate was again evaporated with toluene. There was obtained 8.4 g of β-(aminomethyl)-phenethyl alcohol. The mixture was filtered the filtrate was again evaporated with toluene

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

Procedure: For the preparation of the alcohols VI used in Examples (3a) and (3b). 10 g of 3-amino-2-phenylpropanecarboxylic acid in 150 ml of monoglyme were stirred with 3 g of LiAlH4 for 20 hrs. Then, 12 ml of water and 3 ml of 10% sodium hydroxide solution were slowly added thereto. The mixture was filtered and the filtrate was again evaporated with toluene. There was obtained 8.4 g of β-(aminomethyl)-phenethyl alcohol. The mixture was filtered the filtrate was again evaporated with toluene

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A cooled (0° C.) solution of 3-amino-2-phenylpropan-1-ol (245 mg, 1.62 mmol) in CH2Cl2 (10 mL) was treated with diisopropylethylamine (1.65 mL, 9.72 mmol) and triphosgene (241 mg, 0.81 mmol), under an atmosphere of nitrogen. The reaction was stirred at 0° C. for an additional 2 h. The reaction was quenched with sat. NaHCO3 (2 mL) and then extracted with EtOAc (3×40 mL). The combined organic extracts were washed with brine (30 mL), dried (MgSO4), filtered and concentrated to afford the title compound as a colorless oil. LCMS=178.2 (M+1)+. The reaction was quenched with sat. NaHCO3 (2 mL) extracted with EtOAc (3×40 mL) The combined organic extracts were washed with brine (30 mL) dried (MgSO4) filtered concentrated

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

Procedure: A cooled (0° C.) solution of 2-(3 {[tert-butyl(dimethyl)silyl]oxy}-2-phenylpropyl)-1H-isoindole-1,3(2H)-dione (0.900 g, 2.28 mmol) in EtOH (10 mL) was treated with hydrazine hydrate (1.41 mL, 3.42 mmol) and the resultant solution was allowed to warm to room temperature and stirred for 18 h. A solution of 5 N aqueous HCl in EtOH (25 mL) was added and the resulting biphasic mixture was stirred for 3 h. The mixture was treated with sat. NaHCO3, until PH=9 attained and then extracted with EtOAC (3×60 ml). The combined organic extracts were washed with brine (50 mL), dried (MgSO4), filtered and concentrated to afford the title compound as a white solid. LCMS=152.2 (M+1)+. the resulting biphasic mixture was stirred for 3 h extracted with EtOAC (3×60 ml) The combined organic extracts were washed with brine (50 mL) dried (MgSO4) filtered concentrated

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

Procedure: A cooled (0° C.) solution of 2-(3 {[tert-butyl(dimethyl)silyl]oxy}-2-phenylpropyl)-1H-isoindole-1,3(2H)-dione (0.900 g, 2.28 mmol) in EtOH (10 mL) was treated with hydrazine hydrate (1.41 mL, 3.42 mmol) and the resultant solution was allowed to warm to room temperature and stirred for 18 h. A solution of 5 N aqueous HCl in EtOH (25 mL) was added and the resulting biphasic mixture was stirred for 3 h. The mixture was treated with sat. NaHCO3, until PH=9 attained and then extracted with EtOAC (3×60 ml). The combined organic extracts were washed with brine (50 mL), dried (MgSO4), filtered and concentrated to afford the title compound as a white solid. LCMS=152.2 (M+1)+. the resulting biphasic mixture was stirred for 3 h extracted with EtOAC (3×60 ml) The combined organic extracts were washed with brine (50 mL) dried (MgSO4) filtered concentrated

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

Procedure: Similar procedure as described in example 1b was used, starting from 2-methylsulfanyl-5-[1-quinolin-6-yl-meth-(Z)-ylidene]-thiazol-4-one, 3-hydroxy-2-phenyl-propylamine and DIEA to give 2-(3-hydroxy-2-phenyl-propylamino)-5-[1-quinolin-6-yl-meth-(Z)-ylidene]-thiazol-4-one. LC-MS m/e 390 (MH+).

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To the suspension of ethyl phenylcyanoacetate (1.0 g, 5.3 mmol) in anhydrous ether (200 mL) was added lithium aluminum hydride at 0° C. The mixture was stirred at 0° C. for 18 h. After adding water (1 equiv.), 15% sodium hydroxide (1 equiv.) and water (3 equiv.) to the above solution, the precipitation was removed by filtration. The filtrate was concentrate to dry by lyophilization. Flash chromatography (Merck Silica gel 60, 70-230 mesh, 0%-10% methanol in methylene chloride (0.1% NH4OH) in 30 min afforded 3-hydroxy-2-phenyl-propylamine (0.16 g, 20%). the precipitation was removed by filtration The filtrate was concentrate to dry by lyophilization

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

Procedure: For the preparation of the alcohols VI used in Examples (3a) and (3b). 10 g of 3-amino-2-phenylpropanecarboxylic acid in 150 ml of monoglyme were stirred with 3 g of LiAlH4 for 20 hrs. Then, 12 ml of water and 3 ml of 10% sodium hydroxide solution were slowly added thereto. The mixture was filtered and the filtrate was again evaporated with toluene. There was obtained 8.4 g of β-(aminomethyl)-phenethyl alcohol. The mixture was filtered the filtrate was again evaporated with toluene

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A cooled (0° C.) solution of 3-amino-2-phenylpropan-1-ol (245 mg, 1.62 mmol) in CH2Cl2 (10 mL) was treated with diisopropylethylamine (1.65 mL, 9.72 mmol) and triphosgene (241 mg, 0.81 mmol), under an atmosphere of nitrogen. The reaction was stirred at 0° C. for an additional 2 h. The reaction was quenched with sat. NaHCO3 (2 mL) and then extracted with EtOAc (3×40 mL). The combined organic extracts were washed with brine (30 mL), dried (MgSO4), filtered and concentrated to afford the title compound as a colorless oil. LCMS=178.2 (M+1)+. The reaction was quenched with sat. NaHCO3 (2 mL) extracted with EtOAc (3×40 mL) The combined organic extracts were washed with brine (30 mL) dried (MgSO4) filtered concentrated

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

Procedure: A cooled (0° C.) solution of 2-(3 {[tert-butyl(dimethyl)silyl]oxy}-2-phenylpropyl)-1H-isoindole-1,3(2H)-dione (0.900 g, 2.28 mmol) in EtOH (10 mL) was treated with hydrazine hydrate (1.41 mL, 3.42 mmol) and the resultant solution was allowed to warm to room temperature and stirred for 18 h. A solution of 5 N aqueous HCl in EtOH (25 mL) was added and the resulting biphasic mixture was stirred for 3 h. The mixture was treated with sat. NaHCO3, until PH=9 attained and then extracted with EtOAC (3×60 ml). The combined organic extracts were washed with brine (50 mL), dried (MgSO4), filtered and concentrated to afford the title compound as a white solid. LCMS=152.2 (M+1)+. the resulting biphasic mixture was stirred for 3 h extracted with EtOAC (3×60 ml) The combined organic extracts were washed with brine (50 mL) dried (MgSO4) filtered concentrated