N-Boc-hydroxylamine

[36016-38-3] C5H11NO3 (MW 133.15) InChI = 1S/C5H11NO3/c1-5(2,3)9-4(7)6-8/h8H,1-3H3,(H,6,7) InChIKey = DRDVJQOGFWAVLH-UHFFFAOYSA-N (protecting group incorporation has been used to tune and control the ambident nucleophilicity of hydroxylamine.1N-Boc-hydroxylamine is known to undergo a variety of nucleophilic N- and O-functionalization reactions and is a precursor to tert-butyloxy–nitroso–carbonyl derivatives that can participate as dienophiles in the hetero-Diels–Alder reaction, as enophiles in the ene reaction, and as an electrophilic source of nitrogen or oxygen in the nitrosoformate aldol reaction. One of the most commonly used amino protecting groups, the BOC group, is stable under basic conditions and is readily removed under acidic conditions. As such, N-Boc-hydroxylamine can be readily incorporated into orthogonal protection strategies for organic synthesis) Alternate Names: N-tert-butoxycarbonyl hydroxylamine, tert-butyl N-hydroxycarbamate. Form Supplied in: colorless or beige crystalline solid. Preparative Method: N-Boc-hydroxylamine is commercially available. However, it is easily prepared by stirring a suspension of hydroxylamine hydrochloride (commercially available) and either sodium or potassium carbonate in diethyl ether and water for 1 h.2 Subsequent dropwise addition of tert-butyl dicarbonate (commercially available) in diethyl ether at 0 °C is then followed by stirring at room temperature for 4–16 h. Upon completion, the reaction can be filtered and evaporated to dryness, which is then followed by crystallization in cyclohexane or cyclohexane/toluene to provide the desired product as a crystalline solid. Handling, Storage, and Precautions: appropriate exhaust ventilation is required in areas where dust can be formed. The container must be kept tightly closed in a well-ventilated area, with recommended storage temperature between 2 and 8 °C.