(2R)-2-phenylbutan-1-ol

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

Procedure: To a solution of 4.7 gm of (R)-(−)-2-phenylbutanol (31.78 mmol) and 7.6 mL of pyridine (95 mmol) in 40 mL of CH2Cl2 was added 10 gm of methanesulfonic anhydride (64 mmol). After stirring at room temperature for 5 hr, 100 mL of water was added and the mixture was extracted 3 times with ether. The combined organic fractions were washed with 1N HCl, sat. NaHCO3 and sat. NaCl solutions. The organic fractions were dried over MgSO4, filtered through a thin layer of silica and concentrated in vacuo. The methanesulfonate was used without further purification. 1H NMR (CDCl3) δ 0.85 (t, 3H), 1.65 (m, 2H), 1.85 (m, 2H), 2.75 (s, 3H), 2.9 (m, 1H), 4.35 (d, 2H), 7.3 (m, 5H). A solution of the methanesulfonate, 10 gm of sodium azide (154 mmol) and a trace amount of sodium iodide in 50 mL of DMF was stirred at 80° C. for 12 hr. The reaction mixture was then cooled and 200 mL of ether was added. The mixture was washed 3 times with water, then with sat. NaCl solution, dried over MgSO4, filtered and concentrated. To a solution of the azide in 20 mL of THF was added 50 mL of a 1M solution of LAH in THF and the reaction mixture was stirred at room temperature. After 2 hours, the reaction was quenched with successive additions of 5 mL of water, 5 mL of 10% KOH and 5 mL of water. The aluminum salts were removed by filtration and washed with 200 mL of ethylacetate. The filtrate was dried over MgSO4, filtered and concentrated. The residue was purified by vacuum distillation in a Kugelrohr apparatus (bp 145° C., 0.2 Torr) to give the title compound as a clear liquid. the mixture was extracted 3 times with ether The combined organic fractions were washed with 1N HCl, sat. NaHCO3 and sat. NaCl solutions The organic fractions were dried over MgSO4 filtered through a thin layer of silica concentrated in vacuo The methanesulfonate was used without further purification The reaction mixture was then cooled The mixture was washed 3 times with water with sat. NaCl solution, dried over MgSO4 filtered concentrated To a solution of the azide in 20 mL of THF was added 50 mL of a 1M solution of LAH in THF the reaction mixture was stirred at room temperature After 2 hours the reaction was quenched with successive additions of 5 mL of water, 5 mL of 10% KOH and 5 mL of water The aluminum salts were removed by filtration washed with 200 mL of ethylacetate The filtrate was dried over MgSO4 filtered concentrated The residue was purified by vacuum distillation in a Kugelrohr apparatus (bp 145° C., 0.2 Torr)

Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a suspension of 2.3 gm of LAH (60.6 mmol) in 70 mL of THF was slowly added a solution of 5 gm of (R)-(−)-2-phenylbutyric acid (30.45 mmol, Aldrich) in 30 mL of THF. The reaction mixture was heated to 60° C. for 3 hr. The reaction was cooled to 0° C. and to it was successively added 2 mL of water, 2 mL of 1N KOH and 2 mL of water. The aluminum salts were removed by filtration and washed with 100 mL of ethylacetate. The filtrate was dried over MgSO4, filtered and concentrated to give the title compound which was used without purification. The reaction was cooled to 0° C. and to it The aluminum salts were removed by filtration washed with 100 mL of ethylacetate The filtrate was dried over MgSO4 filtered concentrated

Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a suspension of 2.3 gm of LAH (60.6 mmol) in 70 mL of THF was slowly added a solution of 5 gm of (R)-(−)-2-phenylbutyric acid (30.45 mmol, Aldrich) in 30 mL of THF. The reaction mixture was heated to 60° C. for 3 hr. The reaction was cooled to 0° C. and to it was successively added 2 mL of water, 2 mL of 1N KOH and 2 mL of water. The aluminum salts were removed by filtration and washed with 100 mL of ethylacetate. The filtrate was dried over MgSO4, filtered and concentrated to give the title compound which was used without purification. The reaction was cooled to 0° C. and to it The aluminum salts were removed by filtration washed with 100 mL of ethylacetate The filtrate was dried over MgSO4 filtered concentrated

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

Procedure: To a solution of triphenylphosphine (15.4 g, 59 mmol) and imidazole (3.99 g, 59 mmol) in dichloromethane (150 ml) at room temperature was added portionwise iodine (14.9 g, 50 mmol) at such a rate that the temperature of the reaction mixture did not rise above 30° C. To the mixture was then added a solution of (R)-2-phenyl-butan-1-ol (7.34 g, 41 mmol, CAS 16460-75-6) in dichloromethane (50 ml) and the mixture was then stirred at room temperature overnight. The mixture was then concentrated in vacuo and the residue was resuspended in ether and the resulting crystals collected by filtration. The filtrate was concentrated in vacuo and the residue was triturated in heptane. The resulting crystals were removed by filtration and the filtrate was concentrated in vacuo. The residue was purified by column chromatography (SiO2, heptane/EtOAc) to yield a colourless oil, (6.38 g, 60%). did not rise above 30° C The mixture was then concentrated in vacuo the resulting crystals collected by filtration The filtrate was concentrated in vacuo the residue was triturated in heptane The resulting crystals were removed by filtration the filtrate was concentrated in vacuo The residue was purified by column chromatography (SiO2, heptane/EtOAc) to yield a colourless oil, (6.38 g, 60%)

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

Procedure: To a solution of 4.7 gm of (R)-(−)-2-phenylbutanol (31.78 mmol) and 7.6 mL of pyridine (95 mmol) in 40 mL of CH2Cl2 was added 10 gm of methanesulfonic anhydride (64 mmol). After stirring at room temperature for 5 hr, 100 mL of water was added and the mixture was extracted 3 times with ether. The combined organic fractions were washed with 1N HCl, sat. NaHCO3 and sat. NaCl solutions. The organic fractions were dried over MgSO4, filtered through a thin layer of silica and concentrated in vacuo. The methanesulfonate was used without further purification. 1H NMR (CDCl3) δ 0.85 (t, 3H), 1.65 (m, 2H), 1.85 (m, 2H), 2.75 (s, 3H), 2.9 (m, 1H), 4.35 (d, 2H), 7.3 (m, 5H). A solution of the methanesulfonate, 10 gm of sodium azide (154 mmol) and a trace amount of sodium iodide in 50 mL of DMF was stirred at 80° C. for 12 hr. The reaction mixture was then cooled and 200 mL of ether was added. The mixture was washed 3 times with water, then with sat. NaCl solution, dried over MgSO4, filtered and concentrated. To a solution of the azide in 20 mL of THF was added 50 mL of a 1M solution of LAH in THF and the reaction mixture was stirred at room temperature. After 2 hours, the reaction was quenched with successive additions of 5 mL of water, 5 mL of 10% KOH and 5 mL of water. The aluminum salts were removed by filtration and washed with 200 mL of ethylacetate. The filtrate was dried over MgSO4, filtered and concentrated. The residue was purified by vacuum distillation in a Kugelrohr apparatus (bp 145° C., 0.2 Torr) to give the title compound as a clear liquid. the mixture was extracted 3 times with ether The combined organic fractions were washed with 1N HCl, sat. NaHCO3 and sat. NaCl solutions The organic fractions were dried over MgSO4 filtered through a thin layer of silica concentrated in vacuo The methanesulfonate was used without further purification The reaction mixture was then cooled The mixture was washed 3 times with water with sat. NaCl solution, dried over MgSO4 filtered concentrated To a solution of the azide in 20 mL of THF was added 50 mL of a 1M solution of LAH in THF the reaction mixture was stirred at room temperature After 2 hours the reaction was quenched with successive additions of 5 mL of water, 5 mL of 10% KOH and 5 mL of water The aluminum salts were removed by filtration washed with 200 mL of ethylacetate The filtrate was dried over MgSO4 filtered concentrated The residue was purified by vacuum distillation in a Kugelrohr apparatus (bp 145° C., 0.2 Torr)

Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a suspension of 2.3 gm of LAH (60.6 mmol) in 70 mL of THF was slowly added a solution of 5 gm of (R)-(−)-2-phenylbutyric acid (30.45 mmol, Aldrich) in 30 mL of THF. The reaction mixture was heated to 60° C. for 3 hr. The reaction was cooled to 0° C. and to it was successively added 2 mL of water, 2 mL of 1N KOH and 2 mL of water. The aluminum salts were removed by filtration and washed with 100 mL of ethylacetate. The filtrate was dried over MgSO4, filtered and concentrated to give the title compound which was used without purification. The reaction was cooled to 0° C. and to it The aluminum salts were removed by filtration washed with 100 mL of ethylacetate The filtrate was dried over MgSO4 filtered concentrated