3-[(1S)-1-aminoethyl]phenol

Conditions: temp:37.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A total of 65 g of the 3-hydroxyacetophenone (compound (1)) substrate was charged to the stirred mixture as a powder. After addition of substrate was complete, the volume of the reaction was topped up to 1 L (if necessary) with the appropriate amount of 0.1 M TBA buffer, pH 7.5. The resulting slurry was stirred at 150 rpm at 37° C. (internal temperature). The temperature was monitored using an external temperature probe. The reaction was conducted under a constant nitrogen sweep of 5 L/min. Additional 5 M isopropylamine acetate (100 mL) was charged to the stirred mixture after 24 h and again after 48 h. After addition of substrate

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

Procedure: To a solution of [(S)-1-(3-methoxyphenyl)ethyl]carbamic acid tert-butyl ester (3 g, 12 mmol) in dichloromethane (25 mL) at −78° C. was added BBr3 (1.0 M solution in dichloromethane) (26 mL, 26 mmol) dropwise. After the addition, the solution was warmed up to room temperature. The reaction mixture was quenched with methanol (100 mL) and concentrated under vacuum. This process was repeated until no white fumes were observed upon adding methanol. The title compound was obtained as pale yellow solid (2.6 g, quantitative yield). The crude product was used without any further purification After the addition The reaction mixture was quenched with methanol (100 mL) concentrated under vacuum upon adding methanol

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

Procedure: (S)-[1-(3-Methoxy-phenyl)-ethyl]-carbamic acid tert-butyl ester (50.2 g, 210 mmol) in CH2Cl2 (500 mL) was cooled to −78° C. Boron tribromide (450 mL, 1.0M in CH2Cl2) was added slowly and the resulting mixture was warmed to room temperature and stirred for 3 h. The reaction mixture was again cooled to 0° C. and methanol (500 mL) was added slowly. The solvent was removed in vacuo, and the residue was purified by flash column chromatography on silica gel eluting with 5% MeOH in EtOAc to give the title product in quantitative yield. The reaction mixture was again cooled to 0° C. The solvent was removed in vacuo the residue was purified by flash column chromatography on silica gel eluting with 5% MeOH in EtOAc

Conditions: temp:37.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A total of 65 g of the 3-hydroxyacetophenone (compound (1)) substrate was charged to the stirred mixture as a powder. After addition of substrate was complete, the volume of the reaction was topped up to 1 L (if necessary) with the appropriate amount of 0.1 M TEA buffer, pH 7.5. The resulting slurry was stirred at 150 rpm at 37° C. (internal temperature). The temperature was monitored using an external temperature probe. The reaction was conducted under a constant nitrogen sweep of 5 L/min. Additional 5 M isopropylamine acetate (100 mL) was charged to the stirred mixture after 24 h and again after 48 h. After addition of substrate

Conditions: temp:37.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A total of 65 g of the 3-hydroxyacetophenone (compound (1)) substrate was charged to the stirred mixture as a powder. After addition of substrate was complete, the volume of the reaction was topped up to 1 L (if necessary) with the appropriate amount of 0.1 M TBA buffer, pH 7.5. The resulting slurry was stirred at 150 rpm at 37° C. (internal temperature). The temperature was monitored using an external temperature probe. The reaction was conducted under a constant nitrogen sweep of 5 L/min. Additional 5 M isopropylamine acetate (100 mL) was charged to the stirred mixture after 24 h and again after 48 h. After addition of substrate