Sodium hydride → N-Boc-N-propyl-O-allylhydroxylamine

Temperature

0 °C

N-Boc-O-allylhydroxylamine (6.5 g) from the above procedure was dissolved in dry THF (25 mL) and the solution cooled to 0° C. in an ice bath. Sodium hydride (1.5 g, 60% dispersion in oil) was added portionwise over 5 min. The resulting mixture was stirred for 30 min at 0° C. 1-Iodopropane (3.8 mL) was added dropwise to the mixture. The reaction was stirred at 0° C. for 1 hour, then stirred overnight at room temperature. The THF was removed in vacuo and the residue taken up in EtOAc (50 mL) and washed with water (1×50 mL), saturated sodium bicarbonate solution (3×50 mL), 1N phosphoric acid (3×50 mL), and brine (1×50 mL). The organic layer was dried with sodium sulfate and evaporated to give a light yellow oil, which was purified by flash chromatography on silica gel eluting with 5% EtOAc/hexanes to give the title compound as a colorless oil (6.0 g).

1. stirringThe reaction was stirred at 0° C. for 1 hour
2. stirringstirred overnight at room temperature
3. customThe THF was removed in vacuo
4. washwashed with water (1×50 mL), saturated sodium bicarbonate solution (3×50 mL), 1N phosphoric acid (3×50 mL), and brine (1×50 mL)
5. dry with materialThe organic layer was dried with sodium sulfate
6. customevaporated
7. customto give a light yellow oil, which
8. customwas purified by flash chromatography on silica gel eluting with 5% EtOAc/hexanes

ORD record

ord-35d54636152b416396d59fd6ab5c7e3c

Source dataset

uspto-grants-2005_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06946481B1