Diisobutylaluminum hydride → HCID 66593063, compound

Participants

Reaction Steps

A solution of 3-benzyloxy-2-methylamino-propionitrile (5.0 g) in toluene (90 mL) was cooled to −78° C. and DIBAL-H solution (90 mL of a 20% in toluene) was added drop wise under nitrogen atmosphere. Reaction mixture was slowly warmed to room temperature and then left at stirring for 17 h. The reaction was monitored by TLC. After completion, the reaction mixture was quenched with 10 mL methanol and then 50 mL water. The volatiles where evaporated in vacuo and the crude material was taken up in 50 mL water and acidified to pH=1 with 1M HCl. The aqueous phase was extracted with ethyl acetate and the aqueous layer was subsequently basified to pH=14 with 30% NaOH solution. The free diamine was extracted with dichloromethane, dried over sodium sulfate, filtered and concentrated to afford the desired 3-(benzyloxy)-N2-methylpropane-1,2-diamine (3.8 g) as a brown oil, which was used in the next reaction without further purification. MS (ES+): 195.1 (MH+).

Provenance & Evidence