3-(4-phenylbutoxy)propan-1-ol

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

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

Procedure: To a solution of Intermediate 12 (1.0 g, 4.8 mmol) in CH2Cl2 (20 mL) was added Dess-Martin periodinane (2.4 g, 5.76 mmol) and the reaction was stirred 2 hours at room temperature. The solution was then diluted with CH2Cl2 (40 mL), washed with water (2×20 mL), saturated solution of sodium bicarbonate (2×20 mL), and water (20 mL), dried (Na2SO4), and concentrated. The residue was purified by column chromatography (methylene chloride/acetone, 20:1) to afford the title compound (550 mg, 58%) as oil. washed with water (2×20 mL), saturated solution of sodium bicarbonate (2×20 mL), and water (20 mL) dried (Na2SO4) concentrated The residue was purified by column chromatography (methylene chloride/acetone, 20:1)

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

Procedure: To a solution of Intermediate 12 (1.0 g, 4.8 mmol) in CH2Cl2 (20 mL) was added Dess-Martin periodinane (2.4 g, 5.76 mmol) and the reaction was stirred 2 hours at room temperature. The solution was then diluted with CH2Cl2 (40 mL), washed with water (2×20 mL), saturated solution of sodium bicarbonate (2×20 mL), and water (20 mL), dried (Na2SO4), and concentrated. The residue was purified by column chromatography (methylene chloride/acetone, 20:1) to afford the title compound (550 mg, 58%) as oil. washed with water (2×20 mL), saturated solution of sodium bicarbonate (2×20 mL), and water (20 mL) dried (Na2SO4) concentrated The residue was purified by column chromatography (methylene chloride/acetone, 20:1)

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

Procedure: A solution of Intermediate 11 (0.40 g, 2.10 mmol) in THF (5 mL) was cooled to 0° C. A 0.5 M solution of BBN (5 mL, 2.52 mmol) in THF was added, and the resulting mixture was stirred 1 hour at 0° C. and 2 hours at room temperature. A solution of 2M NaOH (1 mL) and hydrogen peroxide (1 mL, 35%) was successively added and the mixture stirred 1 hour at room temperature. The solution was then concentrated and the residue dissolved in ether (25 mL), washed with water (2×15 mL) and brine (5 mL), dried (Na2SO4) and the solvent removed under reduced pressure. Purification of the residue by column chromatography on silica gel (hexane/AcOEt, 6:1) afforded the title compound (0.24 g, 55%) as oil. the mixture stirred 1 hour at room temperature The solution was then concentrated the residue dissolved in ether (25 mL) washed with water (2×15 mL) and brine (5 mL) dried (Na2SO4) the solvent removed under reduced pressure Purification of the residue by column chromatography on silica gel (hexane/AcOEt, 6:1)

Conditions: temp:0.00; pressure:0.00; stir:

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

Procedure: Obtained from Intermediate 80 (10.6 g, 53 mmol) by the procedure described in Intermediate 12. Purification by column chromatography with silica gel eluting with ethyl acetate/n-hexane (from 1:4 to pute ethyl acetate) gave the title compound (10.7 g, 96%) as oil. Purification by column chromatography with silica gel eluting with ethyl acetate/n-hexane (from 1:4 to pute ethyl acetate)

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

Procedure: To a solution of Intermediate 12 (1.0 g, 4.8 mmol) in CH2Cl2 (20 mL) was added Dess-Martin periodinane (2.4 g, 5.76 mmol) and the reaction was stirred 2 hours at room temperature. The solution was then diluted with CH2Cl2 (40 mL), washed with water (2×20 mL), saturated solution of sodium bicarbonate (2×20 mL), and water (20 mL), dried (Na2SO4), and concentrated. The residue was purified by column chromatography (methylene chloride/acetone, 20:1) to afford the title compound (580 mg, 58%) as oil. washed with water (2×20 mL), saturated solution of sodium bicarbonate (2×20 mL), and water (20 mL) dried (Na2SO4) concentrated The residue was purified by column chromatography (methylene chloride/acetone, 20:1)

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

Procedure: A solution of Intermediate 11 (0.40 g, 2·10 mmol) in THF (5 mL) was cooled to 0° C. A 0.5 M solution of BBN (5 mL, 2.52 mmol) in THF was added, and the resulting mixture was stirred 1 hour at 0° C. and 2 hours at room temperature. A solution of 2M NaOH (1 mL) and hydrogen peroxide (1 ml, 35%) was successively added and the mixture stirred 1 hour at room temperature. The solution was then concentrated and the residue dissolved in ether (25 mL), washed with water (2×15 mL) and brine (15 mL), dried (Na2SO4) and the solvent removed under reduced pressure. Purification of the residue by column chromatography on silica gel (hexane/AcOEt, 6:1) afforded the title compound (0.24 g, 55%) as oil. the mixture stirred 1 hour at room temperature The solution was then concentrated the residue dissolved in ether (25 mL) washed with water (2×15 mL) and brine (15 mL) dried (Na2SO4) the solvent removed under reduced pressure Purification of the residue by column chromatography on silica gel (hexane/AcOEt, 6:1)

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

Procedure: To a solution of Intermediate 12 (1.0 g, 4.8 mmol) in CH2Cl2 (20 mL) was added Dess-Martin periodinane (2.4 g, 5.76 mmol) and the reaction was stirred 2 hours at room temperature. The solution was then diluted with CH2Cl2 (40 mL), washed with water (2×20 mL), saturated solution of sodium bicarbonate (2×20 mL), and water (20 mL), dried (Na2SO4), and concentrated. The residue was purified by column chromatography (methylene chloride/acetone, 20:1) to afford the title compound (550 mg, 58%) as oil. washed with water (2×20 mL), saturated solution of sodium bicarbonate (2×20 mL), and water (20 mL) dried (Na2SO4) concentrated The residue was purified by column chromatography (methylene chloride/acetone, 20:1)

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

Procedure: A solution of Intermediate 11 (0.40 g, 2.10 mmol) in THF (5 mL) was cooled to 0° C. A 0.5 M solution of BBN (5 mL, 2.52 mmol) in THF was added, and the resulting mixture was stirred 1 hour at 0° C. and 2 hours at room temperature. A solution of 2M NaOH (1 mL) and hydrogen peroxide (1 mL, 35%) was successively added and the mixture stirred 1 hour at room temperature. The solution was then concentrated and the residue dissolved in ether (25 mL), washed with water (2×15 mL) and brine (5 mL), dried (Na2SO4) and the solvent removed under reduced pressure. Purification of the residue by column chromatography on silica gel (hexane/AcOEt, 6:1) afforded the title compound (0.24 g, 55%) as oil. the mixture stirred 1 hour at room temperature The solution was then concentrated the residue dissolved in ether (25 mL) washed with water (2×15 mL) and brine (5 mL) dried (Na2SO4) the solvent removed under reduced pressure Purification of the residue by column chromatography on silica gel (hexane/AcOEt, 6:1)