Hydroxyamine hydrochloride → (R)-tert-butyl 2-(4-amino-2-fluorophenyl)morpholine-4-carboxylate

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of (R)-tert-butyl 2-(4-(diphenylmethyleneamino)-2-fluorophenyl)morpholine-4-carboxylate (5.95 g) in methanol (50 ml) were added sodium acetate (2.93 g) and hydroxylamine hydrochloride (1.82 g). The reaction mixture was stirred at 50° C. overnight. The reaction mixture was then filtered through sintered glass and the filtrate was concentrated in vacuo. The residue was purified by flash column chromatography (silica gel; gradient: 0% to 60% EtOAc in hexanes) to afford (R)-tert-butyl 2-(4-amino-2-fluorophenyl)morpholine-4-carboxylate (3.0 g, 85%) as a yellow solid. MS (ISP): 296 ([M]+), 240 ([M-C4H8]+), 195 ([M+H—C4H8—CO2H]+).

Provenance & Evidence