Tetrahydrofuran → HCID 60134460, compound

Participants

Reaction Steps

Sodium hydrogen carbonate (15.0 g, 0.18 mol) dissolved in water (200 mL) was added to reaction containing crude N1-cyclohexyl-N1,3-dimethylbutane-1,3-diamine (14.0 g, 46.1 mmol) was dissolved into THF (200 mL). CbzOSu (11.0 g, 1 equiv, 44.2 mmol) was added in one portion to the reaction and left to stir at room temperature for 16 h. The organic solvent was removed and the aqueous residue was extracted with DCM (3×150 mL). The organic layer was dried over anhydrous MgSO4, filtered and concentrated to a pale yellow oil (12.7 g). The crude oil was purified on an ISCO purification system with gradient elution from 20-100% ethyl acetate then1-10% methanol in ethyl acetate. The desired fraction was collected and concentrated to give a colorless oil (5.27 g, yield: 34.4%). 1H NMR (CDCl3, 400 MHz): δ 1.0-1.49 (m, 5H), 1.37 (s, 6H), 1.55 (t, 2H), 1.6-1.64 (m, 1H), 1.76 (bs, 4H), 2.21 (s, 3H), 2.32-2.4 (m, 1H), 2.60 (t, 2H), 5.03 (s, 2H), 7.2-7.4 (m, 5H), 7.96 (s, 1H). LRMS (ESI+) for C20H32N2O2 (332.3); Found: 333 (MH+).

Provenance & Evidence