Water → HCID 22866039, compound

Participants

Reaction Steps

To a solution of (1S,4S)-2-benzyl-5-ethoxycarbonyl-2,5-diazabicyclo(2.2.1)heptane (3.3 g, 0.013 mol) in THF at -10° C., was added dropwise 1M LiAlH4 in ether (26.3 mL, 0.026 mol). The reaction mixture was slowly warmed to room temperature and mixed overnight. Upon cooling to 0° C., 4 mL of 95% THF:H2O was slowly added followed by 4 mL of H2O. The mixture was diluted with NH4OH (40 mL), filtered through a celite pad and concentrated in vacuo. The remaining NH4OH solution was further diluted with NH4OH (15 mL) and extracted with CH2Cl2. The combined organic phases were dried (K2CO3) and concentrated in vacuo to yield (1S,4S)-2-benzyl-5-methyl-2,5-diazabicyclo(2.2.1)heptane (2.2 g, 86%).

Provenance & Evidence