反应 #1869209

ord-c6bbb2234f50476c840d4ff4dd8187cf

反应方程式

O=[N+]([O-])c1cccc(S(=O)(=O)OC[C@@H]2CO2)c1
(2S)-oxiran-2-ylmethyl-3-nitrobenzenesulfonate
O=C(Cc1ccccc1O)N1CC[C@H](O)C1
(3S)-1-[(2-hydroxyphenyl)acetyl]pyrrolidin-3-ol
O=C([O-])[O-].[Cs+].[Cs+]
Cs2CO3
O=C(Cc1ccccc1OC[C@@H]1CO1)N1CC[C@H](O)C1
subtitled compound
收率 14.3%
O=C(Cc1ccccc1OC[C@@H]1CO1)N1CC[C@H](O)C1
(3S)-1-({2-[(2S)-Oxiran-2-ylmethoxy]phenyl}acetyl)pyrrolidin-3-ol
收率 14.3%

溶剂

反应条件

详细条件
See reaction.notes.procedure_details.

后处理

  1. 1
    其他The reaction mixture was partitioned between ethyl acetate and H2O
  2. 2
    干燥The organic layer was dried over Na2SO4
  3. 3
    过滤filtered
  4. 4
    浓缩concentrated
  5. 5
    其他The residue was purified by silica gel flash chromatography/(0-3% methanol in dichloromethane)

实验过程

A mixture of (2S)-oxiran-2-ylmethyl-3-nitrobenzenesulfonate (228 mg, 0.88 mmol), (3S)-1-[(2-hydroxyphenyl)acetyl]pyrrolidin-3-ol (196 mg, 0.88 mmol) and Cs2CO3 (344 mg, 1.05 mmol) in DMF (5 mL) was stirred at room temperature overnight. The reaction mixture was partitioned between ethyl acetate and H2O. The organic layer was dried over Na2SO4, filtered and concentrated. The residue was purified by silica gel flash chromatography/(0-3% methanol in dichloromethane) to give the subtitled compound (35 mg).

来源

DOI: 10.6084/m9.figshare.5104873.v1专利: US07498338B2uspto-grants-2009_03