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

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 33-3 (0.987 g, 3.19 mmol) in MeOH (32 ml) was treated with Pd/C (0.339 g, 0.319 mmol) under an atmosphere of nitrogen in a three-necked round bottomed flask. The vessel was then briefly evacuated, then backfilled with a balloon containing Hydrogen gas. The reaction was stirred at RT for 2 hours, then filtered through celite, washed with MeOH, followed by dichloromethane. Filtrate was concentrated in vacuo and purified by reverse phase chromatography (C18 column, 5-95% MeCN in water with 0.1% TFA) to yield 33-4. The vessel was then briefly evacuated containing Hydrogen gas filtered through celite washed with MeOH Filtrate was concentrated in vacuo purified by reverse phase chromatography (C18 column, 5-95% MeCN in water with 0.1% TFA) to yield 33-4

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

Procedure: A solution of 33-3 (0.987 g, 3.19 mmol) in MeOH (32 ml) was treated with Pd/C (0.339 g, 0.319 mmol) under an atmosphere of nitrogen in a three-necked round bottomed flask. The vessel was then briefly evacuated, then backfilled with a balloon containing Hydrogen gas. The reaction was stirred at RT for 2 hours, then filtered through celite, washed with MeOH, followed by dichloromethane. Filtrate was concentrated in vacuo and purified by reverse phase chromatography (C18 column, 5-95% MeCN in water with 0.1% TFA) to yield 33-4. The vessel was then briefly evacuated containing Hydrogen gas filtered through celite washed with MeOH Filtrate was concentrated in vacuo purified by reverse phase chromatography (C18 column, 5-95% MeCN in water with 0.1% TFA) to yield 33-4

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 33-3 (0.987 g, 3.19 mmol) in MeOH (32 ml) was treated with Pd/C (0.339 g, 0.319 mmol) under an atmosphere of nitrogen in a three-necked round bottomed flask. The vessel was then briefly evacuated, then backfilled with a balloon containing Hydrogen gas. The reaction was stirred at RT for 2 hours, then filtered through celite, washed with MeOH, followed by dichloromethane. Filtrate was concentrated in vacuo and purified by reverse phase chromatography (C18 column, 5-95% MeCN in water with 0.1% TFA) to yield 33-4. The vessel was then briefly evacuated containing Hydrogen gas filtered through celite washed with MeOH Filtrate was concentrated in vacuo purified by reverse phase chromatography (C18 column, 5-95% MeCN in water with 0.1% TFA) to yield 33-4