反应详情

To a cooled solution of tert-butyl diallylcarbamate (145 mg, 0.74 mmol) in DCM (15 mL) at −78° C. was bubbled ozone for about 5 minutes. The solution was light blue at that point. Excess ozone was removed by flushing nitrogen through the reaction. To the reaction was added methyl(2S)-2-amino-3-(4-nitrophenyl)propanoate hydrochloride and triethylamine (74 mg, 0.74 mmol), followed by NaB(OAc)3H (940 mg, 4.4 mmol). The reaction was allowed to warm to RT, and stir for an additional 4 hours. The mixture was poured into water, extracted with DCM. The organic layer was washed with brine, dried with MgSO4, and purified by prep-TLC (50% EtOAc and Hexanes) to afford 93 mg of the desired tert-butyl 4-[(1S)-2-methoxy-1-(4-nitrobenzyl)-2-oxoethyl]piperazine-1-carboxylate. LC-MS (IE, m/z): 394 [M+1]+.

1. customExcess ozone was removed
2. customby flushing nitrogen
3. customthrough the reaction
4. extractionextracted with DCM
5. washThe organic layer was washed with brine
6. dry with materialdried with MgSO4
7. custompurified by prep-TLC (50% EtOAc and Hexanes)