tert-butyl N-[3-(2-formylphenyl)propyl]carbamate

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

Procedure: A solution of 33-5 (0.385 g, 1.462 mmol) in was treated with methylmagnesium bromide (5.1 ml, 15.3 mmol, 3M in diethylether) at 0° C. After stirring overnight at RT, the reaction was quenched with NH4Cl solution. Extracted with Ethyl acetate, washed with brine and dried over sodium sulfate. Material was purified by reverse phase column chromatography (C18 column, 5-95% MeCN in water with 0.1% TFA) to yield a white solid. Racemic material was separated by chiral chromatography (ChiralTech IC column) to yield 33-6. the reaction was quenched with NH4Cl solution Extracted with Ethyl acetate washed with brine dried over sodium sulfate Material was purified by reverse phase column chromatography (C18 column, 5-95% MeCN in water with 0.1% TFA) to yield a white solid Racemic material was separated by chiral chromatography (ChiralTech IC column) to yield 33-6

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

Procedure: A solution of 33-4 (0.5 g, 1.884 mmol) in dichloromethane (32 ml) was cooled to 0° C. in an ice bath. Dess-Martin Periodinane (1.199 g, 2.83 mmol) was then added in four portions over 20 minutes. After 1 hour, ether was added and the reaction was quenched with 30 mL of 1N NaOH (aq) followed by vigorous stirring for 30 minutes. The layers were then separated. The organic layer was dried over Sodium sulfate, filtered and concentrated in vacuo. The crude material was purified by silica gel column chromatography (0-30% EtOAc in hexane) to yield 33-5. the reaction was quenched with 30 mL of 1N NaOH (aq) The layers were then separated The organic layer was dried over Sodium sulfate filtered concentrated in vacuo The crude material was purified by silica gel column chromatography (0-30% EtOAc in hexane) to yield 33-5

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

Procedure: A solution of 33-5 (0.385 g, 1.462 mmol) in was treated with methylmagnesium bromide (5.1 ml, 15.3 mmol, 3M in diethylether) at 0° C. After stirring overnight at RT, the reaction was quenched with NH4Cl solution. Extracted with Ethyl acetate, washed with brine and dried over sodium sulfate. Material was purified by reverse phase column chromatography (C18 column, 5-95% MeCN in water with 0.1% TFA) to yield a white solid. Racemic material was separated by chiral chromatography (ChiralTech IC column) to yield 33-6. the reaction was quenched with NH4Cl solution Extracted with Ethyl acetate washed with brine dried over sodium sulfate Material was purified by reverse phase column chromatography (C18 column, 5-95% MeCN in water with 0.1% TFA) to yield a white solid Racemic material was separated by chiral chromatography (ChiralTech IC column) to yield 33-6

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

Procedure: A solution of 33-4 (0.5 g, 1.884 mmol) in dichloromethane (32 ml) was cooled to 0° C. in an ice bath. Dess-Martin Periodinane (1.199 g, 2.83 mmol) was then added in four portions over 20 minutes. After 1 hour, ether was added and the reaction was quenched with 30 mL of 1N NaOH (aq) followed by vigorous stirring for 30 minutes. The layers were then separated. The organic layer was dried over Sodium sulfate, filtered and concentrated in vacuo. The crude material was purified by silica gel column chromatography (0-30% EtOAc in hexane) to yield 33-5. the reaction was quenched with 30 mL of 1N NaOH (aq) The layers were then separated The organic layer was dried over Sodium sulfate filtered concentrated in vacuo The crude material was purified by silica gel column chromatography (0-30% EtOAc in hexane) to yield 33-5