反应 #53960

ord-baf8df1b87c8452ebbf4cdc0f2992acd

反应方程式

CC(C)(C)OC(=O)CN[C@H](CO)c1ccccc1
tert-butyl (S)-(2-hydroxy-1-phenyl-ethylamino)-acetate
O=CC(c1ccccc1)c1ccccc1
diphenylacetaldehyde
O=S(=O)([O-])[O-].[Mg+2]
magnesium sulfate
CC(C)(C)OC(=O)CN1C(C(c2ccccc2)c2ccccc2)OC[C@H]1c1ccccc1
tert-butyl ((4R)-2-benzhydryl-4-phenyl-oxazolidin-3-yl)-acetate
收率 114.1%

反应条件

详细条件
See reaction.notes.procedure_details.

后处理

  1. 1
    洗涤The organic layer was washed with saturated sodium chloride solution
  2. 2
    干燥dried over magnesium sulfate
  3. 3
    过滤filtered
  4. 4
    浓缩concentrated to dryness in vacuo
  5. 5
    其他recrystallized from ether/hexanes

实验过程

To a solution of tert-butyl (S)-(2-hydroxy-1-phenyl-ethylamino)-acetate (2.5 g, 10 mmole, obtained from Reference Example 9) in anhydrous methylene chloride (35 ml) were added diphenylacetaldehyde (2.16 g, 11 mmole) and magnesium sulfate (1.2 g, 10 mmole) under nitrogen. The resulting mixture was stirred at room temperature under nitrogen for 15 h, and diluted with ether. The organic layer was washed with saturated sodium chloride solution, dried over magnesium sulfate, filtered and concentrated to dryness in vacuo. The oily residue was solidified upon standing, and recrystallized from ether/hexanes to give tert-butyl ((4R)-2-benzhydryl-4-phenyl-oxazolidin-3-yl)-acetate as a white solid (4.9 g, 98%).

来源

DOI: 10.6084/m9.figshare.5104873.v1专利: US06858591B2uspto-grants-2005_02