Ceric ammonium nitrate → HCID 57979784, compound

Participants

Reaction Steps

(S)-tert-butyl 1-oxopropan-2-ylcarbamate (Boc-L-Alaninal) (3.0 g, 17.32 mmol) and (R)-1-aminopropan-2-ol (1.95 g, 25.98 mmol) in anhydrous methanol (120 mL) was hydrogenated at 1 atmosphere overnight using palladium, 10% wt. on activated carbon (900 mg) as catalyst. Reaction was complete as determined by TLC using CAN spray to visualize. The reaction mixture was then filtered through a celite bed. After solvent evaporation crude product was diluted with ethyl acetate, washed with saturated NAHCO3 (aq.) and dried over MgSO4. Solvent evaporation afforded tert-butyl (S)-1-[(R)-2-hydroxypropylamino]propan-2-ylcarbamate] in 98.5% yield (3.95 g). It was carried to the next step without further purification.

Provenance & Evidence