Benzyl succinimido carbonate → HCID 60134584, compound

Participants

Reaction Steps

Crude 4-(4,4-dimethylpiperidin-1-yl)-2-methylbutan-2-amine (5.80 g, 29.2 mmol) was dissolved into THF (100 mL). To this solution was added CbzOSu (7.29 g, 1 equiv, 29.2 mmol) in one portion. The reaction was left to stir at room temperature for 3 d. The solvent was removed and the residue was taken up in a mixture of diethyl ether (150 mL) and water (50 mL). The layers were separated and the organic layer washed with 1 M sodium carbonate (2×50 mL), 1M HCl (50 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 10-80% ethyl acetate in hexanes. The desired fractions were collected and concentrated to give a white solid (4.75 g, yield: 49.0%). 1H NMR (CDCl3, 400 MHz): δ 0.92 (s, 6H), 1.35-1.40 (bm, 10H), 1.58-1.63 (t, J=10.8, 2 H), 2.40 (bs, 4H), 2.44-2.52 (t, J=10.8, 2H), 5.03 (s, 2H), 7.27-38 (m, 5H). LRMS (ESI+) for C20H32N2O2 (332.2); Found: 333 (MH+).

Provenance & Evidence