反应详情

To a solution of 2-tert-butoxycarbonylamino-2-methyl-3-oxo-propionic acid methyl ester (2.35 g, 6.71 mmol) in methanol (25 mL) was added 4-fluoroaniline (0.53 mL, 5.59 mmol) and acetic acid (0.16 mL, 2.80 mmol). A solution of sodium cyanoborohydride (188 mg, 2.99 mmol) in methanol (25 mL) was added dropwise and the reaction mixture stirred for 3 hours at room temperature post addition. The solvent was removed in vacuo and the residue dissolved in DCM (50 mL). The organic solution was treated with aqueous sodium carbonate solution (20 mL, 1N), stirred for 20 min, and the aqueous layer removed. Concentration of the organic layer followed by purification of the residue using flash chromatography (SiO2, DCM) afforded the title compound as a yellow oil (970 mg, 53%).

1. additionpost addition
2. customThe solvent was removed in vacuo
3. dissolutionthe residue dissolved in DCM (50 mL)
4. additionThe organic solution was treated with aqueous sodium carbonate solution (20 mL, 1N)
5. stirringstirred for 20 min
6. customthe aqueous layer removed
7. customConcentration of the organic layer followed by purification of the residue