huagongshe.com
HRID375428

反应详情

EQUATION

反应方程式

HRID 375428 的结构方程式

REACTANTS

反应物

3
结构：O
HCID962

Water

H2O

结构：[Na+].[OH-]
HCID14798

Sodium Hydroxide

HNaO

结构：COc1ccccc1[C@]1(O)CCC(c2ccccc2)(c2ccccc2)[C@H]2CN(C(=O)[C@@H](OC(C)=O)c3ccccc3)C[C@H]21
HCID22858344

未命名化合物

PRODUCTS

生成物

1
结构：COc1ccccc1[C@]1(O)CCC(c2ccccc2)(c2ccccc2)[C@H]2CN(C(=O)[C@@H](O)c3ccccc3)C[C@H]21
HCID15289533

未命名化合物

收率 80.9%

AUXILIARIES

试剂、催化剂与溶剂

1
结构：CCO
溶剂HCID702

Ethanol

C2H6O

PROCEDURE

实验过程

1.4 cm 3 of an aqueous 1N solution of sodium hydroxide and then 10 cm3 of water are added to a solution of 0.8 g of (3aS,4S,7aS)-7,7-diphenyl-4-(2- methoxyphenyl)-2-[(S)-2-acetyloxy-2-phenylacetyl]perhydroisoindol-4-ol in 30 cm3 of ethanol. The reaction mixture is refluxed for 1 hour and concentrated to dryness under reduced pressure (2.7 kPa), and the residue is taken up in 50 cm3 of water and then 1.5 cm3 of an aqueous 1N solution of hydrochloric acid and extracted with 40 cm3 of ethyl acetate (3 times). The organic phases are combined, washed with 50 cm3 of water, dried over magnesium sulphate and concentrated to dryness under reduced pressure (2.7 kPa). The residue is chromatographed on a Merck silica gel column (particle size 0.04-0.06 mm, diameter 2.5 cm, height 27 cm) by eluting under a pressure of 0.4 bar of nitrogen with a mixture of cyclohexane and ethyl acetate (50/50 by volume) and collecting fractions of 30 cm3. Fractions 2 to 5 are combined and concentrated to dryness under reduced pressure (2.7 kPa). The residue is triturated in isopropyl ether. 0.6 g of (3aS,4S,7aS)-7,7-diphenyl-4-(2-methoxyphenyl)-2-[(S)-2-hydroxy-2-phenylacetyl]perhydroisoindol-4-ol is obtained in the form of white crystals which melt at 256° C.

WORKUP

后处理

  1. temperatureThe reaction mixture is refluxed for 1 hour
  2. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)
  3. extraction1.5 cm3 of an aqueous 1N solution of hydrochloric acid and extracted with 40 cm3 of ethyl acetate (3 times)
  4. washwashed with 50 cm3 of water
  5. dry with materialdried over magnesium sulphate
  6. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)
  7. customThe residue is chromatographed on a Merck silica gel column (particle size 0.04-0.06 mm, diameter 2.5 cm, height 27 cm)
  8. washby eluting under a pressure of 0.4 bar of nitrogen with a mixture of cyclohexane and ethyl acetate (50/50 by volume)
  9. customcollecting fractions of 30 cm3
  10. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)
  11. customThe residue is triturated in isopropyl ether