3-phenylpentane-1,5-diol

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

Procedure: 3.0 g (14.4 mmol) of 3-phenylglutaric acid were dissolved in 20 ml of abs. THF, the mixture was cooled to −10° C. and 31.7 ml (31.7 mmol) of a 1 M solution of lithium aluminium hydride in THF were added dropwise. During the addition, a further 50 ml of abs. THF were added. The resulting suspension was slowly warmed to RT and stirred at RT overnight. After cooling to 0° C., initially isopropanol and then a mixture of isopropanol and water (3:1) were carefully added dropwise. The resulting suspension was acidified by addition of 1 N hydrochloric acid and mixed with Celite. The mixture was filtered through Celite, the filter cake was washed with isopropanol and the filtrate obtained was concentrated under reduced pressure. The crude product was purified by chromatography on silica gel (mobile phase cyclohexane/ethyl acetate 2:1→1:1). This gave 1.9 g of the target product (73% of theory). During the addition After cooling to 0° C. were carefully added dropwise mixed with Celite The mixture was filtered through Celite the filter cake was washed with isopropanol the filtrate obtained was concentrated under reduced pressure The crude product was purified by chromatography on silica gel (mobile phase cyclohexane/ethyl acetate 2:1→1:1)

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

Procedure: 3.0 g (14.4 mmol) of 3-phenylglutaric acid were dissolved in 20 ml of abs. THF, the mixture was cooled to −10° C. and 31.7 ml (31.7 mmol) of a 1 M solution of lithium aluminium hydride in THF were added dropwise. During the addition, a further 50 ml of abs. THF were added. The resulting suspension was slowly warmed to RT and stirred at RT overnight. After cooling to 0° C., initially isopropanol and then a mixture of isopropanol and water (3:1) were carefully added dropwise. The resulting suspension was acidified by addition of 1 N hydrochloric acid and mixed with Celite. The mixture was filtered through Celite, the filter cake was washed with isopropanol and the filtrate obtained was concentrated under reduced pressure. The crude product was purified by chromatography on silica gel (mobile phase cyclohexane/ethyl acetate 2:1→1:1). This gave 1.9 g of the target product (73% of theory). During the addition After cooling to 0° C. were carefully added dropwise mixed with Celite The mixture was filtered through Celite the filter cake was washed with isopropanol the filtrate obtained was concentrated under reduced pressure The crude product was purified by chromatography on silica gel (mobile phase cyclohexane/ethyl acetate 2:1→1:1)

Conditions: temp:180.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 3-Phenylpentane-1,5-diol (452 mg, 2.51 mmol) was dissolved in 48% aqueous hydrobromic acid (284 μL, 2.51 mmol) and toluene (2.5 mL), placed in a sealed tube, and heated in a microwave oven at 180° C. for 10 minutes. The mixture was cooled and purified by column chromatography on silica gel, eluting with 0-100% ethyl acetate/hexanes to give the title compound as a colorless oil. 1H NMR (500 MHz, CDCl3) δ 1.57 (br s, 1H), 1.81-1.97 (m, 2H), 2.08-2.23 (m, 2H), 2.97 (quintet, J=5.0 Hz, 1H), 3.06-3.14 (m, 1H), 3.24-3.31 (m, 1H), 3.42-3.49 (m, 1H), 3.49-3.56 (m, 1H), 7.17-7.25 (m, 3H), 7.28-7.33 (m, 2H). The mixture was cooled purified by column chromatography on silica gel eluting with 0-100% ethyl acetate/hexanes

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 3-Phenylglutaric acid (3.39 g, 16.3 mmol) was dissolved in tetrahydrofuran (163 mL) and cooled to 0° C. A 1.0 M tetrahydrofuran solution of borane tetrahydrofuran complex (65 mL, 65 mmol) was added dropwise, and the reaction was allowed to warm to room temperature overnight. The reaction was cooled to 0° C., quenched with methanol slowly, followed by water, and concentrated in vacuo. The resulting solid was stirred with 1N hydrochloric acid for 20 minutes. The solution was extracted into ethyl acetate. The combined organic layers were dried (magnesium sulfate), filtered, and concentrated in vacuo. The residue was purified by column chromatography on silica gel, eluting with ethyl acetate to give the title compound as a colorless oil. 1H NMR (500 MHz, CDCl3) δ 1.75-1.86 (m, 2H), 1.86-1.96 (m, 2H), 2.45 (br s, 2H), 2.87-2.95 (m, 1H), 3.39-3.48 (m, 2H), 3.49-3.57 (m, 2H), 7.15-7.22 (m, 3H), 7.25-7.31 (m, 2H). to warm to room temperature overnight The reaction was cooled to 0° C. quenched with methanol slowly concentrated in vacuo The solution was extracted into ethyl acetate The combined organic layers were dried (magnesium sulfate) filtered concentrated in vacuo The residue was purified by column chromatography on silica gel eluting with ethyl acetate

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 3-Phenylglutaric acid (3.39 g, 16.3 mmol) was dissolved in tetrahydrofuran (163 mL) and cooled to 0° C. A 1.0 M tetrahydrofuran solution of borane tetrahydrofuran complex (65 mL, 65 mmol) was added dropwise, and the reaction was allowed to warm to room temperature overnight. The reaction was cooled to 0° C., quenched with methanol slowly, followed by water, and concentrated in vacuo. The resulting solid was stirred with 1N hydrochloric acid for 20 minutes. The solution was extracted into ethyl acetate. The combined organic layers were dried (magnesium sulfate), filtered, and concentrated in vacuo. The residue was purified by column chromatography on silica gel, eluting with ethyl acetate to give the title compound as a colorless oil. 1H NMR (500 MHz, CDCl3) δ 1.75-1.86 (m, 2H), 1.86-1.96 (m, 2H), 2.45 (br s, 2H), 2.87-2.95 (m, 1H), 3.39-3.48 (m, 2H), 3.49-3.57 (m, 2H), 7.15-7.22 (m, 3H), 7.25-7.31 (m, 2H). to warm to room temperature overnight The reaction was cooled to 0° C. quenched with methanol slowly concentrated in vacuo The solution was extracted into ethyl acetate The combined organic layers were dried (magnesium sulfate) filtered concentrated in vacuo The residue was purified by column chromatography on silica gel eluting with ethyl acetate

Conditions: temp:180.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 3-Phenylpentane-1,5-diol (452 mg, 2.51 mmol) was dissolved in 48% aqueous hydrobromic acid (284 μL, 2.51 mmol) and toluene (2.5 mL), placed in a sealed tube, and heated in a microwave oven at 180° C. for 10 minutes. The mixture was cooled and purified by column chromatography on silica gel, eluting with 0-100% ethyl acetate/hexanes to give the title compound as a colorless oil. 1H NMR (500 MHz, CDCl3) δ 1.57 (br s, 1H), 1.81-1.97 (m, 2H), 2.08-2.23 (m, 2H), 2.97 (quintet, J=5.0 Hz, 1H), 3.06-3.14 (m, 1H), 3.24-3.31 (m, 1H), 3.42-3.49 (m, 1H), 3.49-3.56 (m, 1H), 7.17-7.25 (m, 3H), 7.28-7.33 (m, 2H). The mixture was cooled purified by column chromatography on silica gel eluting with 0-100% ethyl acetate/hexanes

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 3-Phenylglutaric acid (3.39 g, 16.3 mmol) was dissolved in tetrahydrofuran (163 mL) and cooled to 0° C. A 1.0 M tetrahydrofuran solution of borane tetrahydrofuran complex (65 mL, 65 mmol) was added dropwise, and the reaction was allowed to warm to room temperature overnight. The reaction was cooled to 0° C., quenched with methanol slowly, followed by water, and concentrated in vacuo. The resulting solid was stirred with 1N hydrochloric acid for 20 minutes. The solution was extracted into ethyl acetate. The combined organic layers were dried (magnesium sulfate), filtered, and concentrated in vacuo. The residue was purified by column chromatography on silica gel, eluting with ethyl acetate to give the title compound as a colorless oil. 1H NMR (500 MHz, CDCl3) δ 1.75-1.86 (m, 2H), 1.86-1.96 (m, 2H), 2.45 (br s, 2H), 2.87-2.95 (m, 1H), 3.39-3.48 (m, 2H), 3.49-3.57 (m, 2H), 7.15-7.22 (m, 3H), 7.25-7.31 (m, 2H). to warm to room temperature overnight The reaction was cooled to 0° C. quenched with methanol slowly concentrated in vacuo The solution was extracted into ethyl acetate The combined organic layers were dried (magnesium sulfate) filtered concentrated in vacuo The residue was purified by column chromatography on silica gel eluting with ethyl acetate

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

Procedure: To a suspension of 9.10 g (240 mM) of lithium aluminum hydride in tetrahydrofuran (500 ml)-diethyl ether (200 ml) was added a solution of 24.960 g (119.9 mM) of 3-phenylglutaric acid in 100 ml of tetrahydrofuran dropwise with ice-cooling and the mixture was stirred at room temperature overnight. To this reaction mixture was added water gradually dropwise under ice-cooling until a precipitate had formed. The precipitate was filtered off with the aid of celite and washed with ethyl acetate. The filtrate and washes were pooled and the solvent was distilled off under reduced pressure to provide crude 3-phenylpentane-1,5-diol. This crude product was not purified but used as it was in the next reaction. (Brown liquid, yield 19.19 g). cooling cooling until a precipitate had formed The precipitate was filtered off with the aid of celite washed with ethyl acetate the solvent was distilled off under reduced pressure

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

Procedure: 3.0 g (14.4 mmol) of 3-phenylglutaric acid were dissolved in 20 ml of abs. THF, the mixture was cooled to −10° C. and 31.7 ml (31.7 mmol) of a 1 M solution of lithium aluminium hydride in THF were added dropwise. During the addition, a further 50 ml of abs. THF were added. The resulting suspension was slowly warmed to RT and stirred at RT overnight. After cooling to 0° C., initially isopropanol and then a mixture of isopropanol and water (3:1) were carefully added dropwise. The resulting suspension was acidified by addition of 1 N hydrochloric acid and mixed with Celite. The mixture was filtered through Celite, the filter cake was washed with isopropanol and the filtrate obtained was concentrated under reduced pressure. The crude product was purified by chromatography on silica gel (mobile phase cyclohexane/ethyl acetate 2:1→1:1). This gave 1.9 g of the target product (73% of theory). During the addition After cooling to 0° C. were carefully added dropwise mixed with Celite The mixture was filtered through Celite the filter cake was washed with isopropanol the filtrate obtained was concentrated under reduced pressure The crude product was purified by chromatography on silica gel (mobile phase cyclohexane/ethyl acetate 2:1→1:1)

Conditions: temp:180.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 3-Phenylpentane-1,5-diol (452 mg, 2.51 mmol) was dissolved in 48% aqueous hydrobromic acid (284 μL, 2.51 mmol) and toluene (2.5 mL), placed in a sealed tube, and heated in a microwave oven at 180° C. for 10 minutes. The mixture was cooled and purified by column chromatography on silica gel, eluting with 0-100% ethyl acetate/hexanes to give the title compound as a colorless oil. 1H NMR (500 MHz, CDCl3) δ 1.57 (br s, 1H), 1.81-1.97 (m, 2H), 2.08-2.23 (m, 2H), 2.97 (quintet, J=5.0 Hz, 1H), 3.06-3.14 (m, 1H), 3.24-3.31 (m, 1H), 3.42-3.49 (m, 1H), 3.49-3.56 (m, 1H), 7.17-7.25 (m, 3H), 7.28-7.33 (m, 2H). The mixture was cooled purified by column chromatography on silica gel eluting with 0-100% ethyl acetate/hexanes

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 3-Phenylglutaric acid (3.39 g, 16.3 mmol) was dissolved in tetrahydrofuran (163 mL) and cooled to 0° C. A 1.0 M tetrahydrofuran solution of borane tetrahydrofuran complex (65 mL, 65 mmol) was added dropwise, and the reaction was allowed to warm to room temperature overnight. The reaction was cooled to 0° C., quenched with methanol slowly, followed by water, and concentrated in vacuo. The resulting solid was stirred with 1N hydrochloric acid for 20 minutes. The solution was extracted into ethyl acetate. The combined organic layers were dried (magnesium sulfate), filtered, and concentrated in vacuo. The residue was purified by column chromatography on silica gel, eluting with ethyl acetate to give the title compound as a colorless oil. 1H NMR (500 MHz, CDCl3) δ 1.75-1.86 (m, 2H), 1.86-1.96 (m, 2H), 2.45 (br s, 2H), 2.87-2.95 (m, 1H), 3.39-3.48 (m, 2H), 3.49-3.57 (m, 2H), 7.15-7.22 (m, 3H), 7.25-7.31 (m, 2H). to warm to room temperature overnight The reaction was cooled to 0° C. quenched with methanol slowly concentrated in vacuo The solution was extracted into ethyl acetate The combined organic layers were dried (magnesium sulfate) filtered concentrated in vacuo The residue was purified by column chromatography on silica gel eluting with ethyl acetate

Conditions: temp:180.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 3-Phenylpentane-1,5-diol (452 mg, 2.51 mmol) was dissolved in 48% aqueous hydrobromic acid (284 μL, 2.51 mmol) and toluene (2.5 mL), placed in a sealed tube, and heated in a microwave oven at 180° C. for 10 minutes. The mixture was cooled and purified by column chromatography on silica gel, eluting with 0-100% ethyl acetate/hexanes to give the title compound as a colorless oil. 1H NMR (500 MHz, CDCl3) δ 1.57 (br s, 1H), 1.81-1.97 (m, 2H), 2.08-2.23 (m, 2H), 2.97 (quintet, J=5.0 Hz, 1H), 3.06-3.14 (m, 1H), 3.24-3.31 (m, 1H), 3.42-3.49 (m, 1H), 3.49-3.56 (m, 1H), 7.17-7.25 (m, 3H), 7.28-7.33 (m, 2H). The mixture was cooled purified by column chromatography on silica gel eluting with 0-100% ethyl acetate/hexanes