反应详情

温度

0 °C

The preparation of 4-(4-Benzyloxy-phenylamino)-piperidine-1-carboxylic acid tert-butyl ester (Ia): 4-Benzyloxyaniline hydrochloride salt (10 g, 42.4 mmol) was suspended in EtOAc (500 mL) and washed three times with saturated sodium bicarbonate solution, once with brine, dried over Na2SO4, and concentrated. The free base was dissolved in CH2Cl2 (250 mL), treated with 1-tert-butyl-carbonyl-4-piperidone (8.45 g, 42.4 mmol), stirred for thirty minutes and then cooled to 0° C. NaBH(OAc)3 (13.5 g, 63.6 mmol) was added and the reaction was allowed to warm to room temperature and stir for eighteen hours. The reaction was diluted with CH2Cl2 (250 mL), washed with saturated sodium bicarbonate solution and brine, dried over Na2SO4, and concentrated to give 15.3 g (94%) of the desired product. MS: 383 (M+1 for C23H30N2O3); TLC: SiO2, Rf0.39 (2:1 hexane/EtOAc).

1. washwashed three times with saturated sodium bicarbonate solution
2. dry with materialonce with brine, dried over Na2SO4
3. concentrationconcentrated
4. dissolutionThe free base was dissolved in CH2Cl2 (250 mL)
5. temperatureto warm to room temperature
6. stirringstir for eighteen hours
7. washwashed with saturated sodium bicarbonate solution and brine
8. dry with materialdried over Na2SO4
9. concentrationconcentrated