3-fluoropiperidin-4-one;hydrochloride

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

Procedure: To a suspension of 3-fluoropiperidin-4-one hydrochloride (35.66 g, 232.2 mmol) in THF (800 mL) at 0° C. was added a solution of NaHCO3 (46.81 g, 557.3 mmol) in water (800 mL). After most of the bubbling had subsided the ensuing solution was treated with a solution of naphthalen-2-ylmethyl carbonochloridate (56.36 g, 255.4 mmol) in THF (300 mL) dropwise, over 30 minutes. The mixture was allowed to warm to ambient temperature over 16 hours with vigorous stirring. The mixture was diluted with water and extracted with EtOAc. The combined organic phases were washed with brine, then dried over Na2SO4, filtered arid concentrated. The residue was triturated with methanol and the resulting solid was filtered and dried in vacuo to afford 41.8 g (60%) of desired product as a cream-colored powder. extracted with EtOAc The combined organic phases were washed with brine dried over Na2SO4 filtered arid concentrated The residue was triturated with methanol the resulting solid was filtered dried in vacuo

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

Procedure: To a suspension of 3-fluoropiperidin-4-one hydrochloride (35.66 g, 232.2 mmol) in THF (800 mL) at 0° C. was added a solution of NaHCO3 (46.81 g, 557.3 mmol) in water (800 mL). After most of the bubbling had subsided the ensuing solution was treated with a solution of naphthalen-2-ylmethyl carbonochloridate (56.36 g, 255.4 mmol) in THF (300 mL) dropwise, over 30 minutes. The mixture was allowed to warm to ambient temperature over 16 hours with vigorous stirring. The mixture was diluted with water and extracted with EtOAc. The combined organic phases were washed with brine, then dried over Na2SO4, filtered arid concentrated. The residue was triturated with methanol and the resulting solid was filtered and dried in vacuo to afford 41.8 g (60%) of desired product as a cream-colored powder. extracted with EtOAc The combined organic phases were washed with brine dried over Na2SO4 filtered arid concentrated The residue was triturated with methanol the resulting solid was filtered dried in vacuo

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

Procedure: To a hazy solution of tert-butyl 3-fluoro-4-oxopiperidine-1-carboxylate (52.66 g, 242 mmol) in EtOAc (1 L) was added 4M HCl/dioxane (303 mL, 1212 mmol). The mixture was allowed to stir at ambient temperature for 16 hours. The resulting precipitate was collected by filtration, washed with EtOAc and dried in vacuo to afford 37 g (99%) of desired product as a solid. The resulting precipitate was collected by filtration washed with EtOAc dried in vacuo

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

Procedure: To a suspension of 3-fluoropiperidin-4-one hydrochloride (35.66 g, 232.2 mmol) in THF (800 mL) at 0° C. was added a solution of NaHCO3 (46.81 g, 557.3 mmol) in water (800 mL). After most of the bubbling had subsided the ensuing solution was treated with a solution of naphthalen-2-ylmethyl carbonochloridate (56.36 g, 255.4 mmol) in THF (300 mL) dropwise, over 30 minutes. The mixture was allowed to warm to ambient temperature over 16 hours with vigorous stirring. The mixture was diluted with water and extracted with EtOAc. The combined organic phases were washed with brine, then dried over Na2SO4, filtered arid concentrated. The residue was triturated with methanol and the resulting solid was filtered and dried in vacuo to afford 41.8 g (60%) of desired product as a cream-colored powder. extracted with EtOAc The combined organic phases were washed with brine dried over Na2SO4 filtered arid concentrated The residue was triturated with methanol the resulting solid was filtered dried in vacuo

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

Procedure: To a hazy solution of tert-butyl 3-fluoro-4-oxopiperidine-1-carboxylate (52.66 g, 242 mmol) in EtOAc (1 L) was added 4M HCl/dioxane (303 mL, 1212 mmol). The mixture was allowed to stir at ambient temperature for 16 hours. The resulting precipitate was collected by filtration, washed with EtOAc and dried in vacuo to afford 37 g (99%) of desired product as a solid. The resulting precipitate was collected by filtration washed with EtOAc dried in vacuo