Diethyl Ether → 3-(2-{2-[2-(2-Dimethylamino-ethoxy)-naphthalen-1-yl]-ethoxy}-benzenesulfonylamino)-4-oxo-butyric acid tert-butyl ester

Participants

Reaction Conditions

Reaction Steps

3-(2-{2-[2-(2-Dimethylamino-ethoxy)-naphthalen-1-yl]-ethoxy}-benzenesulfonylamino)-N-methoxy-N-methyl-succinamic acid tert-butyl ester (230 mg, 0.366 mmol) was dissloved in a mixture of freshly distilled THF (0.85 mL) and ether (1.35 mL). The mix was chilled to −65° C. in a dry-ice/chlorofrom bath. LiAlH4 solution (1.23 mL of 1.0 M solution in ether, 1.23 mmol) was added via syringe. The reaction became heterogeneous. Acetonitrile (0.2 mL) and CH2Cl2 (0.2 mL) were added to aid dissolution. The reaction was stirred at −65° C. for 1.25 hours. TLC analysis (5% MeOH/CH2Cl2, silca) indicated the reaction was complete. The reaction was carefully quenched with saturated aqueous KHSO4 (2 mL) and was allowed to warm to room temperature. The reaction was diluted with saturated aqueous NaHCO3 and was extracted three times with EtOAc. The organic extracts were combined, dried over Na2SO4, decanted, and concentrated to give 3-(2-{2-[2-(2-dimethylamino-ethoxy)-naphthalen-1-yl]-ethoxy}-benzenesulfonylamino)-4-oxo-butyric acid tert-butyl ester (202 mg, 0.35 mmol) in 97% yield. MS (APCI) m/z 571.1 (M+1).

Provenance & Evidence