反应详情

To a solution of cis-[4-(tert-butoxycarbonylamino-methyl)-cyclohexylmethyl]-carbamic acid tert-butyl ester (2.55 g, 7.45 mmol) in CH2Cl2 (40 mL) was added 4 M hydrogen chloride in EtOAc (4 mL). The reaction mixture was stirred at ambient temperature for 5 hr and concentrated. The residue was dissolved in 1,4-dioxane (20 mL) and 10% aqueous sodium hydroxide (40 mL) and the resulting solution was cooled on an ice-bath. (Boc)2O (829 mg, 3.80 mmol) was added dropwise and the mixture was stirred at ambient temperature for 3 h. The aqueous layer was extracted with CHCl3 (three times). The combined organic layer was dried over MgSO4, filtered and concentrated, and purified by flash chromatography (silica gel, 9% MeOH in CHCl3) to give cis-(4-aminomethyl-cyclohexylmethyl)-carbamic acid tert-butyl ester (255 mg, 14%) as a pale yellow oil.

1. concentrationconcentrated
2. dissolutionThe residue was dissolved in 1,4-dioxane (20 mL)
3. temperature10% aqueous sodium hydroxide (40 mL) and the resulting solution was cooled on an ice-bath
4. stirringthe mixture was stirred at ambient temperature for 3 h
5. extractionThe aqueous layer was extracted with CHCl3 (three times)
6. dry with materialThe combined organic layer was dried over MgSO4
7. filtrationfiltered
8. concentrationconcentrated
9. custompurified by flash chromatography (silica gel, 9% MeOH in CHCl3)