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HRID1374370

反应详情

EQUATION

反应方程式

HRID 1374370 的结构方程式

REACTANTS

反应物

2
结构：CI
HCID6328

Methyl iodide

CH3I

结构：O=C(N[C@H]1CC[C@@H](O)C[C@H]1COC(c1ccccc1)(c1ccccc1)c1ccccc1)OCc1ccccc1
HCID86596908

未命名化合物

PRODUCTS

生成物

1
结构：CO[C@@H]1CC[C@H](NC(=O)OCc2ccccc2)[C@H](COC(c2ccccc2)(c2ccccc2)c2ccccc2)C1
HCID86596909

未命名化合物

收率 49.1%

AUXILIARIES

试剂、催化剂与溶剂

1
结构：CN(C)C=O
溶剂HCID6228

N,N-Dimethylformamide

C3H7NO

PROCEDURE

实验过程

A sample of benzyl (1S,2R,4R)-4-hydroxy-2-(trityloxymethyl)cyclohexylcarbamate (6.9 g, 13.24 mMol) was dissolved in a mixture of MeI (12.4 mL, 198.6 mMol) and anhydrous DMF (15 mL) prior to the addition of Ag2O (6.1 g, 26.48 mMol) in one portion under an argon flush. The reaction was set to stir at rt in the dark. After stirring for 30 hr (the reaction was incomplete), it was diluted with CH2Cl2 and filtered. through Celite. Filtered and concentrated to a yellow oil and flash chromatographed to get benzyl (1S,2R,4R)-4-methoxy-2-(trityloxymethyl)cyclohexylcarbamate (3.48 g) as a white foamy solid and recover the starting materiel.

WORKUP

后处理

  1. customflush
  2. stirringAfter stirring for 30 hr (the reaction
  3. additionwas diluted with CH2Cl2
  4. filtrationfiltered
  5. filtrationFiltered
  6. concentrationconcentrated to a yellow oil and flash
  7. customchromatographed