(3R)-3-hydroxy-3-phenylpropanenitrile

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

Procedure: To a THF solution of (R)-3-phenyl-3-hydroxypropanenitrile was slowly added 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 (R)-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: To a stirring suspension of lithium aluminum hydride in dry THF at 0° C. was added a solution of (R)-3-phenyl-3-hydroxypropanenitrile in dry THF under nitrogen. The ice bath was removed and then the reaction mixture was refluxed for 2 h. Excess lithium aluminum hydride was destroyed by adding H2O and EtOAc. The white precipitate obtained was filtered and washed with MeOH. The combined filtrate was concentrated to give (R)-3-phenyl-3-hydroxypropylamine. The ice bath was removed the reaction mixture was refluxed for 2 h Excess lithium aluminum hydride was destroyed by adding H2O and EtOAc The white precipitate obtained was filtered washed with MeOH The combined filtrate was concentrated

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

Procedure: To a THF solution of (R)-3-phenyl-3-hydroxypropanenitrile was slowly added borane THF complex at room temperature and then the resulting solution was 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 (R)-3-phenyl-3-hydroxypropylamine. at room temperature the resulting solution was 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: To a THF solution of (R)-3-phenyl-3-hydroxypropanenitrile was slowly added 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 (R)-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