反应详情

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), to a solution of 4-(tert-butoxycarbonyl-amino)butyric acid (1.00 g, 4.77 mmol) in dry CH3CN (24 mL) were added N,O-dimethyl-hydroxylamine hydrochloride (475 mg, 4.77 mmol), EDC.HCl (934 mg, 4.77 mmol), HOBt (658 mg, 4.77 mmol) and N-methylmorpholine (2.68 mL, 23.86 mmol) at rt. The reaction mixture was stirred at rt until completion of the reaction. The mixture was then concentrated under reduced pressure. The residue was redissolved in EA, successively washed with water, 10% aq. KHSO4, sat. aq. NaHCO3 and brine, dried over MgSO4, filtered and concentrated under reduced pressure. The crude material was dissolved in dry THF (20 mL) and treated with MeMgBr (3.0M solution in Et2O, 3.25 mL, 9.75 mmol) at 0° C. The reaction mixture was stirred at 0° C. until completion of the reaction. 10% Aq. KHSO4 was then carefully added, the layers separated and the aq. layer extracted with EA (3×). The combined org. extracts were successively washed with aq. sat. NaHCO3 and brine, dried over MgSO4, filtered and concentrated under reduced pressure. The crude residue was purified by FC (hept-EA 3:2) to give the title compound as a colorless oil. TLC:rf (3:2 hept-EA)=0.38.

1. concentrationThe mixture was then concentrated under reduced pressure
2. dissolutionThe residue was redissolved in EA
3. washsuccessively washed with water, 10% aq. KHSO4, sat. aq. NaHCO3 and brine
4. dry with materialdried over MgSO4
5. filtrationfiltered
6. concentrationconcentrated under reduced pressure
7. dissolutionThe crude material was dissolved in dry THF (20 mL)
8. stirringThe reaction mixture was stirred at 0° C. until completion of the reaction
9. customthe layers separated
10. extractionthe aq. layer extracted with EA (3×)
11. washextracts were successively washed with aq. sat. NaHCO3 and brine
12. dry with materialdried over MgSO4
13. filtrationfiltered
14. concentrationconcentrated under reduced pressure
15. customThe crude residue was purified by FC (hept-EA 3:2)