1-chloro-2-oxidoisoquinolin-2-ium

Conditions: temp:120.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of the compound from Step 2 1-chloroisoquinoline 2-oxide (1.2 g, 6.68 mmol) and tert-butyl (3R)-3-aminopiperidine-1-carboxylate (2.0 g, 10.02 mmol) in n-BuOH (20 mL) was added DIPEA (0.95 g, 7.35 mmol) and DMAP (81 mg, 0.668 mmol). The mixture was stirred at 120° C. for 16 h. The mixture was then poured into water (20 mL) and extracted with EtOAc (3×10 mL). The combined layers organic were dried over Na2SO4, filtered, and the filtrate was concentrated in vacuo. The crude product was purified by silica gel flash column chromatography eluting with a gradient of petroleum ether: EtOAc (1:1 to 0:1) to afford the title compound (0.8 g, 35%). extracted with EtOAc (3×10 mL) The combined layers organic were dried over Na2SO4 filtered the filtrate was concentrated in vacuo The crude product was purified by silica gel flash column chromatography eluting with a gradient of petroleum ether: EtOAc (1:1 to 0:1)

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

Procedure: To a solution of 1-chloroisoquinoline (3.0 g, 18 mmol) in DCM (50 mL) was added m-CPBA (9.5 g, 55 mmol). The mixture was stirred at room temperature for 48 h. The mixture was diluted with DCM, and then washed with brine, dried over Na2SO4, filtered, and the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel flash column chromatography eluting with a gradient of petroleum ether: EtOAc (5:1 to 0:1) to afford the title compound (1.2 g, 36%) as a yellow solid. washed with brine dried over Na2SO4 filtered the filtrate was concentrated under reduced pressure The resulting residue was purified by silica gel flash column chromatography eluting with a gradient of petroleum ether: EtOAc (5:1 to 0:1)

Conditions: temp:120.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of the compound from Step 2 1-chloroisoquinoline 2-oxide (1.2 g, 6.68 mmol) and tert-butyl (3R)-3-aminopiperidine-1-carboxylate (2.0 g, 10.02 mmol) in n-BuOH (20 mL) was added DIPEA (0.95 g, 7.35 mmol) and DMAP (81 mg, 0.668 mmol). The mixture was stirred at 120° C. for 16 h. The mixture was then poured into water (20 mL) and extracted with EtOAc (3×10 mL). The combined layers organic were dried over Na2SO4, filtered, and the filtrate was concentrated in vacuo. The crude product was purified by silica gel flash column chromatography eluting with a gradient of petroleum ether: EtOAc (1:1 to 0:1) to afford the title compound (0.8 g, 35%). extracted with EtOAc (3×10 mL) The combined layers organic were dried over Na2SO4 filtered the filtrate was concentrated in vacuo The crude product was purified by silica gel flash column chromatography eluting with a gradient of petroleum ether: EtOAc (1:1 to 0:1)

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

Procedure: To a solution of 1-chloroisoquinoline (3.0 g, 18 mmol) in DCM (50 mL) was added m-CPBA (9.5 g, 55 mmol). The mixture was stirred at room temperature for 48 h. The mixture was diluted with DCM, and then washed with brine, dried over Na2SO4, filtered, and the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel flash column chromatography eluting with a gradient of petroleum ether: EtOAc (5:1 to 0:1) to afford the title compound (1.2 g, 36%) as a yellow solid. washed with brine dried over Na2SO4 filtered the filtrate was concentrated under reduced pressure The resulting residue was purified by silica gel flash column chromatography eluting with a gradient of petroleum ether: EtOAc (5:1 to 0:1)