Aluminium lithium hydride → tert-butyl N-(2-methyl-3-oxopropyl)carbamate

Participants

Reaction Steps

A solution of LAH (10 mL, 10 mmol, 1M in THF) was slowly added over ˜15 min to a stirred solution of tert-butyl {3-[methoxy(methyl)amino]-2-methyl-3-oxopropyl}carbamate (2.2 g, 8.9 mmol) in THF (40 mL) at −40° C. under nitrogen. After stirring at −40° for 30 min, the reaction mixture was quenched carefully by dropwise addition of saturated aqueous sodium bisulfate solution and stirred at room temperature for 1 hr. The mixture was filtered through Celite, and the filtrate was washed sequentially with ice-cold 1N hydrochloric acid (2×), saturated aqueous sodium bicarbonate and brine, dried over magnesium sulfate, filtered and concentrated to yield tert-butyl (2-methyl-3-oxopropyl)carbamate as colorless viscous oil. MS (M+1−Boc): 88.0

Provenance & Evidence