(1S)-3-amino-1-phenylpropan-1-ol

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

Procedure: To 10 ml of a THF solution of 1.47 g (10.0 mmol) of the (S)-3-hydroxy-3-phenylpropanenitrile obtained in Example 1, slowly added was 1.23 ml (13.0 mmol) of borane.dimethylsulfide complex. After removing the dimethylsulfide by reducing the pressure, the reaction mixture was refluxed for 2.5 hours. The reaction was stopped by the addition of a methanol/hydrochloric acid solution, and the methanol was distilled off under vacuum. After neutralizing with a 5N aqueous solution of sodium hydroxide, the solvent was distilled off, a further aqueous solution of sodium hydroxide was added to make the reaction solution basic, and this was then extracted with methylene chloride. This methylene chloride solution was dried with anhydrous sodium sulfate, and the solvent was then distilled off under vacuum to give 1.47 g of (S)-3-amino-1-phenylpropanol. The amino group of (S)-3-amino-1-phenylpropanol was monobenzoylated by reaction with benzoyl chloride, and when it was analyzed using a CHIRALCEL OB column (manufactured by Daicel Chemical Industries, Ltd., eluant; n-hexane:2-propanol=90:10) it was found that the optical purity was 98% ee. After removing the dimethylsulfide the reaction mixture was refluxed for 2.5 hours The reaction was stopped by the addition of a methanol/hydrochloric acid solution the methanol was distilled off under vacuum the solvent was distilled off a further aqueous solution of sodium hydroxide was added this was then extracted with methylene chloride This methylene chloride solution was dried with anhydrous sodium sulfate the solvent was then distilled off under vacuum

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

Procedure: To a THF solution of (S)-3-phenyl-3-hydroxypropanenitrile was slowly added THF solution of borane dimethyl sulfide complex at room temperature. Methyl sulfide was then distilled from the reaction vessel and the resulting THF solution refluxed for 2.5 h. After cooling to room temperature methanolic HCl was added to the reaction mixture. Methanol and methyl borate were removed by distillation and the reaction mixture neutralized with sodium hydroxide (5N). Extraction of the mixture with dichloromethane,followed by concentration provided the crystalline (S)-3-phenyl-3-hydroxypropylamine. at room temperature Methyl sulfide was then distilled from the reaction vessel the resulting THF solution refluxed for 2.5 h was added to the reaction mixture Methanol and methyl borate were removed by distillation Extraction of the mixture with dichloromethane,followed by concentration

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

Procedure: Following the general method as outlined in Example 22, starting from (2S,4EZ)-1-(tert-butoxycarbonyl)-4-(methoxyimino)-2-pyrrolidinecarboxylic acid, [1,1′-biphenyl]-4-carbonyl chloride, and (1S)-3-amino-1-phenyl-1-propanol, the title compound was obtained in 93% purity by HPLC. MS(ESI+): m/z=472.

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

Procedure: Following the general method as outlined in Example 22, starting from (2S,4EZ)-1-(tert-butoxycarbonyl)-4-(methoxyimino)-2-pyrrolidinecarboxylic acid, 2′-methyl[1,1′-biphenyl]-4-carboxylic acid, and (1S)-3-amino-1-phenyl-1-propanol, the title compound was obtained in 91% purity by HPLC. MS(ESI+): m/z=486.