HRID565423

反应详情

EQUATION

反应方程式

HRID 565423 的结构方程式

PROCEDURE

实验过程

Ethyl 3-methoxybenzoate (10 g, 56 mmol) was dissolved in 55 mL ether, cooled to −78° C., and treated with 55 mL 3.0 M methylmagnesium bromide in ether. The reaction was warmed to room temperature, stirred overnight, and excess reagent was quenched by addition of water and 6 M H2SO4 to the reaction at 0° C. 8.2 g (49 mmol, 89%) of 2-(3-methoxyphenyl)propan-2-ol was obtained as a colorless oil. NMR (1H, CDCl3): 7.25 (m, 1H), 7.07 (m, 2H), 6.79 (m, 1H), 3.80 (s, 3H), 1.56 (s, 6H). The alcohol (8.2 g, 49 mmol) was converted to the azide by the method reported in J. Org. Chem. 1993, 58, 5886. 1.8 g (9.4 mmol, 19%) of 2-(3-methoxyphenyl)propylazide was obtained. NMR (1H, CDCl3) 7.5-6.7 (m, 4H), 3.8 (s, 3H), 1.55 (s, 6H). The azide (1.8 g, 9.4 mmol) was reduced to the amine with catalytic 10% Pd/C, H2 (40 psi), and 5 mL conc. HCl in 75 mL ethanol. 1.5 g (9.3 mmol, 99%) of 2-(3-methoxyphenyl)propyl-2-amine was obtained as an oil. MS (Cl) m/z 166 (MH+). The amine was converted to the amide with (R,R)-2-phenylcyclopropanecarboxylic acid, then reduced to the amine using the method in example 2.