2-phenylpropane-1,2-diol

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

Procedure: To a solution of 2-phenylpropane-1,2-diol (300 mg, 1.972 mmol) in DCM (60 mL) was added Dess-Martin periodinane (836 mg, 1.972 mmol) at 0° C. The reaction mixture was then stirred for 2 hours at room temperature. After completion of reaction (monitored by TLC (TLC eluent: 50% EtOAc in petroleum ether, UV active)), the reaction mixture was quenched with saturated NaHCO3 solution and extracted with EtOAc. The combined organic layers were washed with water, saturated NaCl solution and dried over anhydrous Na2SO4. The solvents were removed under reduced pressure providing 2-hydroxy-2-phenylpropanal (250 g) as a colorless liquid, which was used without further purification. the reaction mixture was quenched with saturated NaHCO3 solution extracted with EtOAc The combined organic layers were washed with water, saturated NaCl solution dried over anhydrous Na2SO4 The solvents were removed under reduced pressure

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

Procedure: To a solution of 2-phenylpropane-1,2-diol (3 g, 19.7 mmol) in DCM (60 mL) was added Dess-Martin periodinane (8.36 g, 19.7 mmol) at 0° C. The reaction mixture was stirred for 2 hours at ambient temperature. After completion of the reaction (monitored by TLC (TLC eluent: 30% EtOAc in petroleum ether)), the reaction mixture was quenched with saturated NaHCO3 solution and extracted with EtOAc. The organic layers were combined and washed with water, washed with saturated NaCl solution, and dried on anhydrous Na2SO4. The organic layer was then filtered and concentrated under vacuum to yield intermediate 2-hydroxy-2-phenylpropanal (2 g unpurified) as a colorless liquid. The intermediate thus obtained was used in the next step without any further purification. 1H NMR (400 MHz, CDCl3): δ 9.50 (s, 1H). The 1H NMR spectrum was not completely clean, but since the aldehyde peak at 9.50 ppm was observed, this intermediate was used in the next step without purification. the reaction mixture was quenched with saturated NaHCO3 solution extracted with EtOAc washed with water washed with saturated NaCl solution dried on anhydrous Na2SO4 The organic layer was then filtered concentrated under vacuum

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

Procedure: To a solution of in prop-1-en-2-ylbenzene (commercially available from Sigma-Aldrich, Milwaukee, Wis.) (2 g, 16.9 mmol) in a THF (20 mL): H2O (10 mL) mixture were added N-methylmorpholine N-oxide (1.98 g, 16.9 mmol) and osmium tetroxide (429.90 mg, 1.6 mmol) at 0° C. The resulting reaction mixture was stirred for 2 hours at ambient temperature. After completion of reaction (monitored by TLC (TLC eluent: 30% EtOAc in petroleum ether)), the reaction mixture was diluted with water and extracted with EtOAc. The organic layers were combined and washed with water, washed with saturated NaCl solution, and dried on anhydrous Na2SO4. Then the organic layer was filtered and concentrated under vacuum to provide a residue which was purified by column chromatography eluting with 50-60% EtOAc in hexane to afford 2-phenylpropane-1,2-diol, 1.5 g (58.25%) as a colorless liquid. 1H NMR (400 MHz, DMSO-d6): δ 7.45-7.43 (m, 2H), 7.30-7.26 (m, 2H), 7.20-7.16 (m, 1H), 4.86 (s, 1H), 4.68 (t, J=6 Hz, 1H), 3.39 (d, J=6 Hz, 1H), 1.38 (s, 3H). (no MS ionization). The resulting reaction mixture extracted with EtOAc washed with water washed with saturated NaCl solution dried on anhydrous Na2SO4 Then the organic layer was filtered concentrated under vacuum to provide a residue which was purified by column chromatography eluting with 50-60% EtOAc in hexane

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

Procedure: To a solution of in prop-1-en-2-ylbenzene (commercially available from Sigma-Aldrich, Milwaukee, Wis.) (2 g, 16.9 mmol) in a THF (20 mL): H2O (10 mL) mixture were added N-methylmorpholine N-oxide (1.98 g, 16.9 mmol) and osmium tetroxide (429.90 mg, 1.6 mmol) at 0° C. The resulting reaction mixture was stirred for 2 hours at ambient temperature. After completion of reaction (monitored by TLC (TLC eluent: 30% EtOAc in petroleum ether)), the reaction mixture was diluted with water and extracted with EtOAc. The organic layers were combined and washed with water, washed with saturated NaCl solution, and dried on anhydrous Na2SO4. Then the organic layer was filtered and concentrated under vacuum to provide a residue which was purified by column chromatography eluting with 50-60% EtOAc in hexane to afford 2-phenylpropane-1,2-diol, 1.5 g (58.25%) as a colorless liquid. 1H NMR (400 MHz, DMSO-d6): δ 7.45-7.43 (m, 2H), 7.30-7.26 (m, 2H), 7.20-7.16 (m, 1H), 4.86 (s, 1H), 4.68 (t, J=6 Hz, 1H), 3.39 (d, J=6 Hz, 1H), 1.38 (s, 3H). (no MS ionization). The resulting reaction mixture extracted with EtOAc washed with water washed with saturated NaCl solution dried on anhydrous Na2SO4 Then the organic layer was filtered concentrated under vacuum to provide a residue which was purified by column chromatography eluting with 50-60% EtOAc in hexane

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

Procedure: Prepared according to the procedure described in Example 48, Step 2, using 1-[4′-(4-bromomethyl-3-methyl-isoxazol-5-yl)-biphenyl-4-yl]-cyclopropanecarboxylic acid ethyl ester and 2-phenyl-propane-1,2-diol. Prepared

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

Procedure: Prepared according to the procedure described in Example 17, Step 2, using 1-[4′-(4-bromomethyl-3-methyl-isoxazol-5-yl)-biphenyl-4-yl]-cyclopropanecarboxylic acid ethyl ester and 2-phenyl-propane-1,2-diol. Prepared

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

Procedure: To a solution of 2-phenylpropane-1,2-diol (300 mg, 1.972 mmol) in DCM (60 mL) was added Dess-Martin periodinane (836 mg, 1.972 mmol) at 0° C. The reaction mixture was then stirred for 2 hours at room temperature. After completion of reaction (monitored by TLC (TLC eluent: 50% EtOAc in petroleum ether, UV active)), the reaction mixture was quenched with saturated NaHCO3 solution and extracted with EtOAc. The combined organic layers were washed with water, saturated NaCl solution and dried over anhydrous Na2SO4. The solvents were removed under reduced pressure providing 2-hydroxy-2-phenylpropanal (250 g) as a colorless liquid, which was used without further purification. the reaction mixture was quenched with saturated NaHCO3 solution extracted with EtOAc The combined organic layers were washed with water, saturated NaCl solution dried over anhydrous Na2SO4 The solvents were removed under reduced pressure

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

Procedure: To a solution of 2-phenylpropane-1,2-diol (3 g, 19.7 mmol) in DCM (60 mL) was added Dess-Martin periodinane (8.36 g, 19.7 mmol) at 0° C. The reaction mixture was stirred for 2 hours at ambient temperature. After completion of the reaction (monitored by TLC (TLC eluent: 30% EtOAc in petroleum ether)), the reaction mixture was quenched with saturated NaHCO3 solution and extracted with EtOAc. The organic layers were combined and washed with water, washed with saturated NaCl solution, and dried on anhydrous Na2SO4. The organic layer was then filtered and concentrated under vacuum to yield intermediate 2-hydroxy-2-phenylpropanal (2 g unpurified) as a colorless liquid. The intermediate thus obtained was used in the next step without any further purification. 1H NMR (400 MHz, CDCl3): δ 9.50 (s, 1H). The 1H NMR spectrum was not completely clean, but since the aldehyde peak at 9.50 ppm was observed, this intermediate was used in the next step without purification. the reaction mixture was quenched with saturated NaHCO3 solution extracted with EtOAc washed with water washed with saturated NaCl solution dried on anhydrous Na2SO4 The organic layer was then filtered concentrated under vacuum

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

Procedure: To a solution of in prop-1-en-2-ylbenzene (commercially available from Sigma-Aldrich, Milwaukee, Wis.) (2 g, 16.9 mmol) in a THF (20 mL): H2O (10 mL) mixture were added N-methylmorpholine N-oxide (1.98 g, 16.9 mmol) and osmium tetroxide (429.90 mg, 1.6 mmol) at 0° C. The resulting reaction mixture was stirred for 2 hours at ambient temperature. After completion of reaction (monitored by TLC (TLC eluent: 30% EtOAc in petroleum ether)), the reaction mixture was diluted with water and extracted with EtOAc. The organic layers were combined and washed with water, washed with saturated NaCl solution, and dried on anhydrous Na2SO4. Then the organic layer was filtered and concentrated under vacuum to provide a residue which was purified by column chromatography eluting with 50-60% EtOAc in hexane to afford 2-phenylpropane-1,2-diol, 1.5 g (58.25%) as a colorless liquid. 1H NMR (400 MHz, DMSO-d6): δ 7.45-7.43 (m, 2H), 7.30-7.26 (m, 2H), 7.20-7.16 (m, 1H), 4.86 (s, 1H), 4.68 (t, J=6 Hz, 1H), 3.39 (d, J=6 Hz, 1H), 1.38 (s, 3H). (no MS ionization). The resulting reaction mixture extracted with EtOAc washed with water washed with saturated NaCl solution dried on anhydrous Na2SO4 Then the organic layer was filtered concentrated under vacuum to provide a residue which was purified by column chromatography eluting with 50-60% EtOAc in hexane