Methylhydrazine → (S)-4-tert-butyl 1-(4-methoxybenzyl) 2-(aminooxy)succinate

Participants

Reaction Steps

To a solution of (S)-4-tert-butyl 1-(4-methoxybenzyl) 2-((1,3-dioxoisoindolin-2-yl)oxy)succinate (68 g, 149 mmol) in Dichloromethane (DCM) (500 mL) was added methylhydrazine (7.86 mL, 149 mmol) dropwise at 0° C. over 30 min. The mixture was allowed to warm to rt and stirred at rt for 1 h. LCMS indicated completion of the reaction. The insoluble material was removed by filtration and the filtrate was concentrated and diluted with toluene. The resulting precipitate was removed by filtration again and the filtrate was concentrated to afford crude (S)-4-tert-butyl 1-(4-methoxybenzyl) 2-(aminooxy)succinate (47 g, 144 mmol, 97% yield) as a pale yellow oil. The product was used in next step without further purification. LCMS: (M+H)+: 326.1

Provenance & Evidence