反应详情

To an ice-cold, stirred solution of (1S,2R)-2-(1-adamantylmethylamino)-1-phenylpropan-1-ol (715 mg, 2.4 mmol) and DIEA (1.3 mL, 7.2 mmol) in CH2Cl2 (50 mL) was added solid triphosgene (233 mg, 0.79 mmol). The ice bath was allowed to melt and the mixture was stirred at rt for 3 h. The mixture was diluted with ether (150 mL), washed with 5% aq HCl (50 mL) and satd aq NaHCO3 (50 mL), and dried over MgSO4. Removal of the solvent left (4R,5S)-3-((1-adamantyl)methyl)-4-methyl-5-phenyloxazolidin-2-one as a white solid. 1H NMR (CDCl3) 0.76 (d, 3H), 1.5-1.8 (12H), 2.01 (3H), 2.52 (d, 1H), 3.30 (d, 1H), 4.09 (m, 1H), 5.63 (d, 1H), 7.25-7.40 (5H); LC-MS (3 min) tR=2.26 min, m/z=326, 348.

1. washwashed with 5% aq HCl (50 mL)
2. dry with materialdried over MgSO4
3. customRemoval of the solvent
4. waitleft (4R,5S)-3-((1-adamantyl)methyl)-4-methyl-5-phenyloxazolidin-2-one as a white solid
5. customLC-MS (3 min) tR=2.26 min, m/z=326, 348