Tpc-A014 synthesis

Yield:54149-39-2 88%

Reaction Conditions:

with hydrazine in methanol at 20;Heating / reflux;

Steps:

120

To a suspension of the phthalimide (2.13 g, 9.64 mmol) in MeOH (57 ml) was added hydrazine hydrate (0.4 ml, 12.86 mmol) and the mixture heated to reflux for 4 h then cooled to rt and stirred overnight. The reaction was filtered, concentrated and diluted with Et₂O (30 ml). The Et₂O layer was filtered and concentrated and re-diluted with Et₂O (30 ml). The Et₂O was filtered again and concentrated to afford 0-(2-methoxy-ethyl)-hydroxylamine (775 mg, 88%) as a pale yellow oil. ¹H NMR (CDCl₃) 6 3.38 (s, 3H), 3.55-3.58 (m, 2H), 3.81-3.84 (m, 2H), 4.25 (br s, 2H).

References:

WO2006/138350,2006,A2 Location in patent:Page/Page column 143