2-(oxan-4-ylamino)phenol

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

Procedure: A solution of intermediate D7 (0.66 g, 3.415 mmol) and N-bromosuccinimide (0.669 g, 3.757 mmol) in DMF (10 ml) was stirred at r.t. for 1 h. Subsequently, the r.m. was washed with an aqueous saturated NaHCO3 solution. The organic layer was separated, dried (Na2SO4), filtered and the solvent evaporated in vacuo. The crude product was purified by column chromatography (silica gel; DCM/EtOAc 8:2 as eluent). The desired fractions were collected and evaporated in vacuo to yield D9 (0.433 g, 46.6%) as a reddish solid. was washed with an aqueous saturated NaHCO3 solution The organic layer was separated dried (Na2SO4) filtered the solvent evaporated in vacuo The crude product was purified by column chromatography (silica gel; DCM/EtOAc 8:2 as eluent) The desired fractions were collected evaporated in vacuo

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

Procedure: A solution of intermediate D7 (0.66 g, 3.415 mmol) and N-bromosuccinimide (0.669 g, 3.757 mmol) in DMF (10 ml) was stirred at r.t. for 1 h. Subsequently, the r.m. was washed with an aqueous saturated NaHCO3 solution. The organic layer was separated, dried (Na2SO4), filtered and the solvent evaporated in vacuo. The crude product was purified by column chromatography (silica gel; DCM/EtOAc 8:2 as eluent). The desired fractions were collected and evaporated in vacuo to yield D9 (0.433 g, 46.6%) as a reddish solid. was washed with an aqueous saturated NaHCO3 solution The organic layer was separated dried (Na2SO4) filtered the solvent evaporated in vacuo The crude product was purified by column chromatography (silica gel; DCM/EtOAc 8:2 as eluent) The desired fractions were collected evaporated in vacuo

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

Procedure: A mixture of 2-aminophenol (1 g, 9.164 mmol), tetrahydropyran-4-one (1.099 ml, 11.913 mmol), and sodium triacetoxy-borohydride (0.71 g, 3.42 mmol) in DCE (50 ml) was stirred at r.t. for 16 h. The crude was filtered over diatomaceous earth, washed with DCM and the filtrate was evaporated in vacuo to yield D7 (0.69 g) that was used as such in the next reaction step without further purification. The crude was filtered over diatomaceous earth washed with DCM the filtrate was evaporated in vacuo

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

Procedure: A mixture of 2-aminophenol (1 g, 9.164 mmol), tetrahydropyran-4-one (1.099 ml, 11.913 mmol), and sodium triacetoxy-borohydride (0.71 g, 3.42 mmol) in DCE (50 ml) was stirred at r.t. for 16 h. The crude was filtered over diatomaceous earth, washed with DCM and the filtrate was evaporated in vacuo to yield D7 (0.69 g) that was used as such in the next reaction step without further purification. The crude was filtered over diatomaceous earth washed with DCM the filtrate was evaporated in vacuo

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

Procedure: A mixture of 2-aminophenol (1 g, 9.164 mmol), tetrahydropyran-4-one (1.099 ml, 11.913 mmol), and sodium triacetoxyborohydride (0.71 g, 3.42 mmol) in DCE (50 ml) was stirred at room temperature for 16 h. The crude mixture was filtered over diatomaceous earth, washed with DCM and the filtrate was evaporated in vacuo to yield D2O (0.69 g) which was used as such in the next reaction step without further purification. The crude mixture was filtered over diatomaceous earth washed with DCM the filtrate was evaporated in vacuo to yield D2O (0.69 g) which such in the next reaction step without further purification

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

Procedure: A mixture of 2-aminophenol (1 g, 9.164 mmol), tetrahydropyran-4-one (1.099 ml, 11.913 mmol), and sodium triacetoxyborohydride (0.71 g, 3.42 mmol) in DCE (50 ml) was stirred at room temperature for 16 h. The crude mixture was filtered over diatomaceous earth, washed with DCM and the filtrate was evaporated in vacuo to yield D2O (0.69 g) which was used as such in the next reaction step without further purification. The crude mixture was filtered over diatomaceous earth washed with DCM the filtrate was evaporated in vacuo to yield D2O (0.69 g) which such in the next reaction step without further purification