2-phenylpropan-1-ol

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

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

Procedure: The title compound, white solid, m.p. 131° C. and MS: m/e=373.5 (M+H+) was prepared in accordance with the general method of example 1 from diphenylacetyl isocyanate and (RS)-2-phenyl-propan-1-ol.

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

Procedure: Following the procedures analogous to that used for the preparation of 4-((S)-2-fluoro-1-methyl-ethyl)-benzenesulfonyl chloride, but starting with 2-phenyl-1-propanol in step a.3.g.1, the title compound was prepared.

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

Procedure: A mixture of (4S)-4-(phenylmethyl)-3-(2-phenylpropionyl)-2-oxazolidinone (XLI, Isomer I, 2.651 g, 8.57 mmol) in THF (10 ml) is added dropwise to a cooled slurry of lithium aluminum hydride (0.3518 g, 9.27 mmol) in THF (10 ml). After the mixture had stirred for 28 min at 0°, water (0.35 ml) is added and the mixture is stirred for 15 min. Sodium hydroxide (15% aqueous solution, 0.35 ml) is added and again the mixture is allowed to stir for 15 min. After the final addition of water (1.05 ml), the salts are removed by filtration and washed with ether. The combined filtrates are washed with saline, dried over magnesium sulfate and concentrated. The residue is chromatographed on silica gel eluting with ethyl acetate/hexane (15/85). The appropriate fractions are pooled and concentrated to give 2-phenylpropanol (XLIII, Isomer Ia), NMR (CDCl3) 1.28, 1.35, 2.95, 3.71 and 7.26 δ. the mixture is stirred for 15 min to stir for 15 min the salts are removed by filtration washed with ether The combined filtrates are washed with saline dried over magnesium sulfate concentrated The residue is chromatographed on silica gel eluting with ethyl acetate/hexane (15/85) concentrated

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

Procedure: The same reaction as in Example 1 (1b) was conducted using N-(4-hydroxybenzoyl)glycine tert-butyl ester (247 mg, 0.983 mmol) prepared in Example 1 (1a) and 2-phenylpropan-1-ol (185 μL, 1.32 mmol) to give 221 mg of the title compound (white powder, yield: 72%).

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

Procedure: Using the method described in Example 1(b), 1.2 parts per hour of a 50 percent strength by weight solution of 2-methyl-2-phenyl-3-hydroxypropanal in a 1:1 water-methanol mixture are hydrogenated, over the catalyst prepared as described in Example 1(a), at 130° C. and 30 bar, with a throughput of 0.3 part of 2-methyl-2-phenyl-3-hydroxypropanol per liter of catalyst per hour. The conversion is over 99 percent. The hydrogenated material is fractionated through a packed column. After first runnings of water, methanol, 2-phenylpropanol and 2-methyl-2-phenyl-3-hydroxypropanal, 2-methyl-2-phenyl-propane-1,3-diol, of boiling point 143°-145° C./1 mbar (melting point 80°-82° C.), is obtained in an amount corresponding to 0.5405 part per hour. This is equivalent to a yield of 89% of theory, based on starting material. prepared as described in Example 1(a), at 130° C.

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

Procedure: The title compound, white solid, m.p. 131° C. and MS: m/e=373.5 (M+H+) was prepared in accordance with the general method of example 1 from diphenylacetyl isocyanate and (RS)-2-phenyl-propan-1-ol.

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

Procedure: The title compound, white solid, m.p. 131° C. and MS: m/e=373.5 (M+H+) was prepared in accordance with the general method of example 1 from diphenylacetyl isocyanate and (RS)-2-phenyl-propan-1-ol.

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

Procedure: Following the procedures analogous to that used for the preparation of 4-((S)-2-fluoro-1-methyl-ethyl)-benzenesulfonyl chloride, but starting with 2-phenyl-1-propanol in step a.3.1, the title compound was prepared.

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

Procedure: The subtitle compound (14.95 g) was prepared according to the procedure in example 6 part a using 2-phenyl-1-propanol (13.6 g), t-butylbromoacetate (19.5 g), tetrabutylammoniumbromide (3.2 g), toluene (70 ml), 50% aqueous sodium hydroxide (25 ml).

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

Procedure: The same reaction as in Example 1 (1b) was conducted using N-(4-hydroxybenzoyl)glycine tert-butyl ester (247 mg, 0.983 mmol) prepared in Example 1 (1a) and 2-phenylpropan-1-ol (185 μL, 1.32 mmol) to give 221 mg of the title compound (white powder, yield: 72%).

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

Procedure: Following the procedures analogous to that used for the preparation of 4-((S)-2-fluoro-1-methyl-ethyl)-benzenesulfonyl chloride, but starting with 2-phenyl-1-propanol in step a.3.1, the title compound was prepared.