Tetrahydrofuran → HCID 57447696, compound

Participants

Reaction Steps

A suspension of 3-methoxyazetidine (275) (MacKenzie et al., PCT Int. Appl. WO 9605193, 1996) (1.6 g, 18.8 mmol), 2-(3-bromopropyl)phthalimide (4.8 g, 17.9 mmol) and K2CO3 (3.7 g, 26.9 mmol) in THF (150 mL) was stirred at reflux temperature for 18 h. The solution was cooled, the solvent evaporated and the residue partitioned between water (50 mL) and EtOAc (100 mL). The aqueous layer was extracted with EtOAc (2×150 mL), the combined organic fraction washed with water (2×100 mL) and brine (100 mL), dried and the solvent evaporated. The residue was purified by chromatography, eluting with a gradient (0-5%) of MeOH/DCM, to give phthalimide 300 (5.2 g, 65%) as a colourless oil: 1H NMR δ 7.84 (dd, J=5.4, 3.1 Hz, 2H, Harom), 7.70 (dd, J=5.4, 3.1 Hz, 2H, Harom), 3.95 (p, J=5.8 Hz, 1H, CHO), 3.73 (t, J=7.1 Hz, 2H, CH2N), 3.55-3.60 (m, 2H, CH2N), 3.22 (s, 3H, OCH3), 2.78-2.84 (m, 2H, CH2N), 2.51 (t, J=7.1 Hz, 2H, CH2N), 1.72 (p, J=7.1 Hz, 2H, CH2); MS (APCI) m/z 275 (MH+, 100%); HRMS (FAB+) calcd for C15H19N2O3 (MH+) m/z 275.1396, found 275.1391.

Provenance & Evidence