2-[(2R)-4-hydroxybutan-2-yl]isoindole-1,3-dione

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

Procedure: To a solution of 2,6-dichlorophenol (14.9 mg, 0.0910 mmol) in THF (1.5 mL) was added (R)-2-(4-hydroxybutan-2-yl)isoindoline-1,3-dione (20 mg, 0.091 mmol) and triphenylphosphine (47.9 mg, 0.182 mmol) and the reaction mixture was cooled to 0° C. in an ice/water bath. DIAD (0.035 mL, 0.18 mmol) was added drop wise and the reaction mixture was stirred at 0° C. for 1 h. The reaction mixture was allowed to warm to rt and stirred at rt for 16 h. The reaction mixture was concentrated under vacuum to yield a yellow oil that was purified by flash chromatography. Intermediate 8A (0.10 g, 96% yield) was isolated as a clear oil. LC-MS (ESI) 365 (M+H), RT=2.84 min (Method A). to warm to rt stirred at rt for 16 h The reaction mixture was concentrated under vacuum to yield a yellow oil that was purified by flash chromatography

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

Procedure: To a solution of 2,6-dichlorophenol (14.9 mg, 0.0910 mmol) in THF (1.5 mL) was added (R)-2-(4-hydroxybutan-2-yl)isoindoline-1,3-dione (20 mg, 0.091 mmol) and triphenylphosphine (47.9 mg, 0.182 mmol) and the reaction mixture was cooled to 0° C. in an ice/water bath. DIAD (0.035 mL, 0.18 mmol) was added drop wise and the reaction mixture was stirred at 0° C. for 1 h. The reaction mixture was allowed to warm to rt and stirred at rt for 16 h. The reaction mixture was concentrated under vacuum to yield a yellow oil that was purified by flash chromatography. Intermediate 8A (0.10 g, 96% yield) was isolated as a clear oil. LC-MS (ESI) 365 (M+H), RT=2.84 min (Method A). to warm to rt stirred at rt for 16 h The reaction mixture was concentrated under vacuum to yield a yellow oil that was purified by flash chromatography

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

Procedure: To a solution of 2,6-dichlorophenol (14.9 mg, 0.091 mmol) in THF (1.5 mL) was added (R)-2-(4-hydroxybutan-2-yl)isoindoline-1,3-dione (20 mg, 0.091 mmol) and triphenylphosphine (47.9 mg, 0.182 mmol) and the reaction mixture was cooled to 0° C. in an ice/water bath. DIAD (0.035 mL, 0.182 mmol) was added drop wise and the reaction mixture was stirred at 0° C. for 1 h. The reaction mixture was allowed to warm to rt and was stirred at rt overnight. The reaction mixture was concentrated under vacuum to yield a yellow oil that was diluted with a minimal amount of DCM, loaded onto a 12 g ISCO column and purified by ISCO. Intermediate 13A (0.1003 g, 96% yield) was isolated as a clear oil. LC-MS (ESI) 365 (M+H), RT=2.84 min (Method A). NMR indicated that the final product contained reduced DIAD. to warm to rt was stirred at rt overnight The reaction mixture was concentrated under vacuum to yield a yellow oil that purified by ISCO

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

Procedure: To a solution of 2,6-dichlorophenol (14.9 mg, 0.0910 mmol) in THF (1.5 mL) was added (R)-2-(4-hydroxybutan-2-yl)isoindoline-1,3-dione (20 mg, 0.091 mmol) and triphenylphosphine (47.9 mg, 0.182 mmol) and the reaction mixture was cooled to 0° C. in an ice/water bath. DIAD (0.035 mL, 0.18 mmol) was added drop wise and the reaction mixture was stirred at 0° C. for 1 h. The reaction mixture was allowed to warm to rt and stirred at rt for 16 h. The reaction mixture was concentrated under vacuum to yield a yellow oil that was purified by flash chromatography. Intermediate 8A (0.10 g, 96% yield) was isolated as a clear oil. LC-MS (ESI) 365 (M+H), RT=2.84 min (Method A). to warm to rt stirred at rt for 16 h The reaction mixture was concentrated under vacuum to yield a yellow oil that was purified by flash chromatography