Borane;tetrahydrofuran → (2S)-1-(1-Benzhydryl-azetidin-3-ylamino)-3-(4-benzyloxy-phenoxy)-propan-2-ol

Participants

Reaction Steps

To a solution of (2S)-1-(1-Benzhydryl-azetidin-3-ylideneamino)-3-(4-benzyloxy-phenoxy)-propan-2-ol (0.49 g, 1 mmol) in tetrahydrofuran (4 ml) was added 1.2 ml of borane-tetrahydrofuran (1.0 M in THF), and the mixture was stirred at room temperature for 20 h. It was then quenched with 1.5 ml of 2 N NaOH, and the volatiles were evaporated. The aqueous solution was removed, and the residue was washed with water, and treated with 3 ml of 2 N HCL and 3 ml of methanol for 20 h. The mixture was then made alkaline with 1 N NaOH, and the methanol was evaporated. The resulting suspension was filtered, and the precipitate washed with water, and dried in vacuo to give 0.46 g of a white solid; m.p. 109-110°C.; MS (ES) m/z 495.7 (MH+); HRMS (El) Calcd. for C32H34N2O3 (M+): 494.2570, Found: 494.2561.

Provenance & Evidence