反应详情

To a solution of (1-adamantylmethyl)amine (15 g, 52 mmol) in anhydrous CH2Cl2 (50 mL) was added tert-butyl 2-((tert-butyldimethylsilyloxy)methyl)aziridine-1-carboxylate (13 g, 78.3 mmol). The mixture was stirred for 10 min, the solvent was removed in vacuo and the residue was stirred at 40° C. for 5 h. The mixture was diluted with EtOAc (500 mL) and washed with water (100 mL),1N aq HCl (50 mL), satd aq NaHCO3 (50 ml) and brine (50 mL), and dried over MgSO4. The solution was concentrated to give a residue, which was purified by chromatography on silica gel to give (S)-tert-butyl 1-(tert-butyldimethylsilyloxy)-3-((1-adamantylmethyl)amino)propan-2-ylcarbamate (10 g, 24%). 1H NMR: (CDCl3, 400 MHz): δ=0.041 (s, 6H), 0.882 (s, 9H), 1.44 (s, 9H), 1.49 (s, 6H), 1.65 (m, 6H), 1.94 (s, 3H), 2.23 (s, 2H), 2.62-2.81 (m, 2H), 3.67 (m, 3H), 5.30 (s, 1H).

1. customthe solvent was removed in vacuo
2. stirringthe residue was stirred at 40° C. for 5 h
3. additionThe mixture was diluted with EtOAc (500 mL)
4. washwashed with water (100 mL),1N aq HCl (50 mL)
5. dry with materialdried over MgSO4
6. concentrationThe solution was concentrated
7. customto give a residue, which
8. customwas purified by chromatography on silica gel