反应 #607484

ord-16a0ee398f064e169779dcbf380e0c14

反应方程式

O=C([O-])O.[Na+]
sodium bicarbonate
CC(C)(C)OC(=O)C1CC(C)(C)C(=O)N1C(=O)OC(C)(C)C
137c
CC(C)(C)OC(=O)C1CC(C)(C)C(=O)N1C(=O)OC(C)(C)C
di-tert-butyl 4,4-dimethyl-5-oxopyrrolidine-1,2-dicarboxylate
CC(C)(C)OC(=O)C1CC(C)(C)C(O)N1C(=O)OC(C)(C)C
di-tert-butyl 5-hydroxy-4,4-dimethylpyrrolidine-1,2-dicarboxylate

溶剂

反应条件

详细条件
See reaction.notes.procedure_details.

后处理

  1. 1
    workup.STIRRINGstirred for 30 min
  2. 2
    萃取extracted with DCM (1 L×3)
  3. 3
    洗涤The combined organic extracts were washed with brine (1 L×3)
  4. 4
    干燥dried over anhydrous sodium sulfate
  5. 5
    过滤filtered
  6. 6
    浓缩concentrated under reduced pressure

实验过程

Et3BHLi (134 mL, 134 mmol, 1M in THF) was added slowly to a mixture of 137c (35 g, 112 mmol) in THF (1 L) at −78° C. and stirred for 2 h. See FIG. 1. Saturated aqueous sodium bicarbonate solution (500 mL) was added, stirred for 30 min, then extracted with DCM (1 L×3). The combined organic extracts were washed with brine (1 L×3), dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure to give di-tert-butyl 5-hydroxy-4,4-dimethylpyrrolidine-1,2-dicarboxylate 137d as a colorless oil (38 g, crude).

来源

DOI: 10.6084/m9.figshare.5104873.v1专利: US09326985B2uspto-grants-2016_05