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HRID1747644

反应详情

EQUATION

反应方程式

HRID 1747644 的结构方程式

REACTANTS

反应物

3
结构：CN(C)C=O
HCID6228

N,N-Dimethylformamide

C3H7NO

结构：[N-]=[N+]=[N-].[Na+]
HCID33557

未命名化合物

结构：CC(C)(C)[Si](C)(C)O[C@H]1C[C@@H](OS(C)(=O)=O)C[C@H]1CO
HCID86618728

(1S,2S,4S)-2-[[(1,1-Dimethylethyl)dimethylsilyl]oxy]-4-[(methylsulfonyl)oxy]cyclopentanemethanol

C13H28O5SSi

PRODUCTS

生成物

1
结构：CC(C)(C)[Si](C)(C)O[C@H]1C[C@H](N=[N+]=[N-])C[C@H]1CO
HCID59671297

未命名化合物

CONDITIONS

反应条件

温度
55 °C

PROCEDURE

实验过程

To a solution of (1S,3S,4S)-3-{[tert-butyl(dimethyl)silyl]oxy}-4-(hydroxymethyl)-cyclopentyl methanesulfonate (0.470 g, 0.00145 mol) in N,N-Dimethylformamide (6 mL, 0.08 mol) was added sodium azide (0.4 g, 0.006 mol) 23° C., and the mixture was heated at 55° C. for 3 hours. The reaction was cooled to 23° C., quenched by addition of water and extracted with Et2O (3×), dried (Na2SO4), filtered and concentrated. The residue was purified by flash chromatography (10 to 25% ethyl acetate/hexane) to obtain 211 mg (53.7%).

WORKUP

后处理

  1. temperatureThe reaction was cooled to 23° C.
  2. customquenched by addition of water
  3. extractionextracted with Et2O (3×)
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by flash chromatography (10 to 25% ethyl acetate/hexane)
  8. customto obtain 211 mg (53.7%)