2-[(2S)-1-hydroxypropan-2-yl]isoindole-1,3-dione

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

Procedure: Using 4-fluoro-5-methylisoxazol-3-ol and 2-[(1S)-2-hydroxy-1-methylethyl]-1H-isoindole-1,3(2H)-dione, and in the same manner as in Example 1, step B, the title compound was obtained.

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

Procedure: Using 4-fluoro-5-methylisoxazol-3-ol and 2-[(1S)-2-hydroxy-1-methylethyl]-1H-isoindole-1,3(2H)-dione, and in the same manner as in Example 1, step B, the title compound was obtained.

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

Procedure: Using 5-bromo-3-fluoropyridin-2-ol and 2-((2S)-1-hydroxypropan-2-yl)-1H-isoindole-1,3(2H)-dione, and in the same manner as in Step C of Example 1, the title compound was obtained.

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

Procedure: Using 5-bromo-3-fluoropyridin-2-ol and 2-((2S)-1-hydroxypropan-2-yl)-1H-isoindole-1,3(2H)-dione, and in the same manner as in Step C of Example 1, the title compound was obtained.

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

Procedure: To a solution of 2-[(1S)-2-hydroxy-1-methyl-ethyl]isoindoline-1,3-dione (47 g, 229 mmol) and iodoethane (89.3 g, 572.5 mmol) in THF (376 mL) is added potassium tert-butoxide (64.25 g, 572.5 mmol) in one portion. The mixture is stirred under a nitrogen atmosphere for 15 h. The mixture is diluted with ethyl acetate (200 mL) and washed with brine (200 mL). The aqueous phase is extracted with ethyl acetate (2×100 mL). The combined organic extracts are dried over MgSO4, filtered, concentrated under reduced pressure, and then dried under high vacuum to afford the title compound (39.4 g, 74%) as an orange solid that is used without further purification. LC-ES/MS m/z 234 (M+1). washed with brine (200 mL) The aqueous phase is extracted with ethyl acetate (2×100 mL) The combined organic extracts are dried over MgSO4 filtered concentrated under reduced pressure dried under high vacuum

Conditions: temp:140.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of (2S)-2-aminopropan-1-ol (26 mL, 333 mmol) and phthalic anhydride (51.7 g, 349.4 mmol) is heated at 140° C. overnight. During this time the solid becomes an orange liquid. The reaction is cooled to RT and diluted with ethyl acetate (10 mL/g). The organic phase is washed with saturated NaHCO3 and 10% citric acid, dried over MgSO4, filtered, and concentrated to afford the title compound (68.3 g, 98%) as a white solid that is used without further purification. LC-ES/MS m/z 206 (M+1). The reaction is cooled to RT The organic phase is washed with saturated NaHCO3 and 10% citric acid dried over MgSO4 filtered concentrated

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

Procedure: Using 4-fluoro-5-methylisoxazol-3-ol and 2-[(1S)-2-hydroxy-1-methylethyl]-1H-isoindole-1,3(2H)-dione, and in the same manner as in Example 1, step B, the title compound was obtained.