(S)-(+)-2-(N-MethylaMino)-3-phenylpropanol

Conditions: temp:-10.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a suspension of N-methyl-L-phenylalanine (20 g, 112 mmol) in THF (1200 mL) cooled to −10° C. was added in small portions lithium aluminium hydride (6.35 g, 167 mmol). After ceasing of the initial exothermic reaction, the cooling bath was removed and the reaction mixture was heated at reflux overnight. Subsequently, another portion of lithium aluminium hydride (4.24 g, 112 mmol) was added after cooling to −10° C., followed by refluxing for an additional 3 h. The reaction mixture was cooled to −40° C., and aqueous 2 N sodium hydroxide was added cautiously. After warming up to r.t., the mixture was filtered, the residue was washed with MTB, and the filtrate was evaporated to give the crude target compound (17.7 g, 96% yield) which was used without further purification. exothermic reaction the cooling bath was removed the reaction mixture was heated at reflux overnight after cooling to −10° C. by refluxing for an additional 3 h The reaction mixture was cooled to −40° C. After warming up to r.t. the mixture was filtered the residue was washed with MTB the filtrate was evaporated

Conditions: temp:-5.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of N-methyl-L-phenylalanine (Sigma, 10 g, 55.8 mmol) in dry THF (600 mL) was added 3.18 g (83.7 mmol) lithium aluminium hydride at −5° C. The reaction mixture was stirred over night and cooled to −5° C. Additional 2.12 g (55.8 mmol) lithium alanate were added. The reaction mixture was refluxed overnight and cooled then to −5° C. To this mixture was added 21.5 ml NaOH solution (2N) drop by drop. and stirred at room temperature for additional 30 min. The mixture was filtered and the filtercake was washed with diethyl ether (50 mL). The filtrate was dried over MgSO4 and solvent was removed under reduced pressure to obtain the product 1b as light yellow solid. The reaction mixture was refluxed overnight cooled to −5° C and stirred at room temperature for additional 30 min The mixture was filtered the filtercake was washed with diethyl ether (50 mL) The filtrate was dried over MgSO4 and solvent was removed under reduced pressure

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

Procedure: Compound 1c is synthesized according to general procedure H from starting material 1b using 2.5 mmol of propargyl bromide (298 mg). The desired compound is obtained in 60% yield (243 mg, 1.2 mmol). Compound 1c is synthesized

Conditions: temp:-10.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a suspension of N-methyl-L-phenylalanine (20 g, 112 mmol) in THF (1200 mL) cooled to −10° C. was added in small portions lithium aluminium hydride (6.35 g, 167 mmol). After ceasing of the initial exothermic reaction, the cooling bath was removed and the reaction mixture was heated at reflux overnight. Subsequently, another portion of lithium aluminium hydride (4.24 g, 112 mmol) was added after cooling to −10° C., followed by refluxing for an additional 3 h. The reaction mixture was cooled to −40° C., and aqueous 2 N sodium hydroxide was added cautiously. After warming up to r.t., the mixture was filtered, the residue was washed with MTB, and the filtrate was evaporated to give the crude target compound (17.7 g, 96% yield) which was used without further purification. exothermic reaction the cooling bath was removed the reaction mixture was heated at reflux overnight after cooling to −10° C. by refluxing for an additional 3 h The reaction mixture was cooled to −40° C. After warming up to r.t. the mixture was filtered the residue was washed with MTB the filtrate was evaporated