5-Azido-5-(2-methoxyphenyl)-1-pentene → 5-Amino-5-(2-methoxyphenyl)-1-pentene

Participants

Reaction Steps

To a solution of 5-azido-5-(2-methoxyphenyl)-1-pentene (1.59 g. 7.33 mmol) in anhydrous ether (10 mL) at 0° C. was added to LiAlH4 in diethyl ether (1.0M, 7.33 mL) dropwise over a period of 20 minutes. The ice bath was removed and the reaction mixture was kept at room temperature for 25 minutes. The reaction solution was cooled to 0° C. to 40° C. and saturated Na2SO4 solution was added dropwise until no hydrogen gas was evolved. Anhydrous Na2SO4 was added followed by diethyl ether (70 mL), the resulting suspension was stirred at room temperature for 1 hour and the solution was then filtered through a pad of Celite™. The filtrate was evaporated to give the title compound (1.63 g) as a colorless oil, which was used for the Preparation 19 without purification. 1H NMR (CDCl3, 400 MHz) δ: 7.22 (2H), 6.93 (3H), 5.80 (1H), 4.92 (2H), 4.13 (1H), 3.82 (3H, OMe), 1.2-2.2 (6H).

Provenance & Evidence