3-(4-aminophenyl)propan-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: The title compound was prepared from 3-(4-amino phenyl)-propan-1-ol (1.02 g, 6.72 mmol) and acrylic acid 2,2,2-trichloroethylester (4.55 g, 22.17 mmol) in the same manner as described for 2-chloro-3-(4-hydroxymethyl-phenyl)-propionic acid methyl ester. The crude product was purified by flash chromatography using DCM/iPrOH 95:5 as the eluent and the product was obtained as an oil (0.74 g, 29.4%). 1H NMR (300 MHz, CDCl3): δ 7.08-7.30 (m, 4H), 4.56-4.60 (t, 1H), 3.63-3.65 (m, 3H), 3.35-3.43 (dd, 1H), 3.18-3.25 (dd, 1H), 2.63-2.68 (m, 3H), 1.84-1.86 (m, 2H). The crude product was purified by flash chromatography

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

Procedure: To a mixture of 3-(4-amino-phenyl)-propionic acid (1.85 g, 11.2 mmol) and tetrahydrofuran′(200 ml), was added lithium aluminum hydride (1.0 g, 26 mmol). After stirring for 3 hours, the mixture was quenched by addition of methanol (5 ml) and concentrated under reduced pressure. The residue was treated with saturated aqueous sodium chloride solution (100 ml) and extracted with ethyl acetate (200 ml). The organic extract was concentrated under reduced pressure to give 3-(4-amino-phenyl)-propan-1-ol (1.5 g, 89% yield). the mixture was quenched by addition of methanol (5 ml) concentrated under reduced pressure The residue was treated with saturated aqueous sodium chloride solution (100 ml) extracted with ethyl acetate (200 ml) The organic extract 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 mixture of 3-(4-amino-phenyl)-propionic acid (1.85 g, 11.2 mmol) and tetrahydrofuran′(200 ml), was added lithium aluminum hydride (1.0 g, 26 mmol). After stirring for 3 hours, the mixture was quenched by addition of methanol (5 ml) and concentrated under reduced pressure. The residue was treated with saturated aqueous sodium chloride solution (100 ml) and extracted with ethyl acetate (200 ml). The organic extract was concentrated under reduced pressure to give 3-(4-amino-phenyl)-propan-1-ol (1.5 g, 89% yield). the mixture was quenched by addition of methanol (5 ml) concentrated under reduced pressure The residue was treated with saturated aqueous sodium chloride solution (100 ml) extracted with ethyl acetate (200 ml) The organic extract was concentrated under reduced pressure

Conditions: temp:22.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a round bottomed flask equipped with a magnetic stirrer was added 4-nitrocinnamyl alcohol (2.0 g, 11.16 mmol), 10% Pd on carbon (200 mg) and absolute ethanol (150 mL). The solution was purged with hydrogen and stirred at 22° C. under a hydrogen atmosphere. When TLC indicated the reaction was complete (4 h), the solution was purged with argon and filtered through Celite. The filtrate was concentrated in vacuo to provide 3-(4-aminophenyl)propanol, 1.72 g (>100%), as a viscous oil which solidified on standing. To a round bottomed flask equipped with a magnetic stirrer The solution was purged with hydrogen (4 h) the solution was purged with argon filtered through Celite The filtrate was concentrated in vacuo

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

Procedure: To a round bottomed flask was added the 3-(4-aminophenyl)propanol (1.3 g, 8.6 mmol), pyridine (1.0 mL, 12 mmol) and dichloromethane (25 mL). The solution was cooled to 0° C. and treated with allyl chloroformate (1.0 mL, 9.4 mmol). After allowing to warm to 22° C. over 1 hour, the reaction mixture was diluted with dichloromethane and washed twice with 1N HCl, followed by sat. NaHCO3, water and sat. aq. NaCl. The organic extract was dried (MgSO4) and concentrated in vacuo. Purification by flash chromatography (50% EtOAc in hexane), provided 1.77 g (88%) of 3-(4-(N-carboallyloxy)aminophenyl)propanol as a clear oil which solidified on standing. to warm to 22° C. over 1 hour washed twice with 1N HCl The organic extract was dried (MgSO4) concentrated in vacuo Purification by flash chromatography (50% EtOAc in hexane)

Conditions: temp:22.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a round bottomed flask equipped with a magnetic stirrer was added 4-nitrocinnamyl alcohol (2.0 g, 11.16 mmol), 10% Pd on carbon (200 mg) and absolute ethanol (150 mL). The solution was purged with hydrogen and stirred at 22° C. under a hydrogen atmosphere. When TLC indicated the reaction was complete (4 hr), the solution was purged with argon and filtered through Celite. The filtrate was concentrated in vacuo to provide 3-(4-aminophenyl)propanol, 1.72 g (>100%), as a viscous oil which solidified on standing. To a round bottomed flask equipped with a magnetic stirrer The solution was purged with hydrogen (4 hr) the solution was purged with argon filtered through Celite The filtrate was concentrated in vacuo

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

Procedure: To a round bottomed flask was added the 3-(4-aminophenyl)propanol (1.3 g, 8.6 mmol), pyridine (1.0 mL, 12 mmol) and dichloromethane (25 mL). The solution was cooled to 0° C. and treated with allyl chloroformate (1.0 mL, 9.4 mmol). After allowing to warm to 22° C. over 1 hour, the reaction mixture was diluted with dichloromethane and washed twice with 1N HCl, followed by sat. NaHCO3, water and sat. aq. NaCl. The organic extract was dried (MgSO4) and concentrated in vacuo. Purification by flash chromatography (50% EtOAc in hexane), provided 1.77 g (88%) of 3-(4-(N-carboallyloxy)aminophenyl)propanol as a clear oil which solidified on standing. to warm to 22° C. over 1 hour washed twice with 1N HCl The organic extract was dried (MgSO4) concentrated in vacuo Purification by flash chromatography (50% EtOAc in hexane)

Conditions: temp:22.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a round bottomed flask equipped with a magnetic stirrer was added 4-nitrocinnamyl alcohol (2.0 g, 11.16 mmol), 10% Pd on carbon (200 mg) and absolute ethanol (150 mL). The solution was purged with hydrogen and stirred at 22° C. under a hydrogen atmosphere. When TLC indicated the reaction was complete (4 hr), the solution was purged with argon and filtered through Celite. The filtrate was concentrated in vacuo to provide 3-(4-aminophenyl)propanol, 1.72 g (>100%), as a viscous oil which solidified on standing. To a round bottomed flask equipped with a magnetic stirrer The solution was purged with hydrogen (4 hr) the solution was purged with argon filtered through Celite The filtrate was concentrated in vacuo

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

Procedure: To a 50 mL round bottomed flask was added 1H-imidazole (59.4 mg, 0.873 mmol), 3-(4-aminophenyl)propan-1-ol 120 mg, 0.794 mmol) and Tetrahydrofuran (THF) (5 mL). To this solution was added tert-butylchlorodimethylsilane (132 mg, 0.873 mmol), and this was left to stir for 2 days, under nitrogen at room temperature. Another 0.5 eq of tert-butylchlorodimethylsilane was added to the reaction and the reaction was left to stir for another 2 hours. After this, reaction was stopped and the suspension concentrated down on a Biotage V10 evaporator, and then the product extracted to the organic phase of an aqueous work up between ethyl acetate (10 mL) and water (10 mL). The organic phase was then passed through a hydrophobic frit, and concentrated in vacuo, leaving the crude product (212 mg, 100%). LCMS (M+1): 266, RT 1.14 mins. this was left the reaction was left to stir for another 2 hours After this, reaction the suspension concentrated down on a Biotage V10 evaporator the product extracted to the organic phase of an aqueous work up between ethyl acetate (10 mL) and water (10 mL) concentrated in vacuo