Benzyl succinimido carbonate → HCID 60134461, compound

Participants

Reaction Steps

Crude N1,N1-dibutyl-3-methylbutane-1,3-diamine (10.18 g, 47.4 mmol) was dissolved into THF (237 mL, 0.2 M). To this solution was added CbzOSu (11.8 g, 1 equiv, 47.4 mmol) in one portion. The reaction was left to stir at room temperature for 17 h. The solvent was removed and the residue was taken up in a mixture of ethyl acetate (600 mL) and water (200 mL). The layers were separated and the organic layer washed with water (2×300 mL) and brine (100 mL). The organic layer was dried over anhydrous MgSO4, filtered and concentrated to a pale yellow oil. The crude oil was purified on an ISCO purification system with gradient elution from 60-80% ethyl acetate in hexanes. The desired fractions were collected and concentrated to give a colorless oil (12.6 g, 76.3%). LRMS (ESI+) for C21H36N2O2 (348.3); Found: 349 (MH+).

Provenance & Evidence