Sodium Hydroxide → HCID 86755049, compound

HRID 324658Notes

Reaction equation

HRID 324658 reaction equation
FC(F)(F)S(O)(=O)=O.[CH2:9]([N:16]1[CH2:24][C:23]2([C:25]([O:27][CH3:28])=[O:26])[CH:18]([C:19](O)([C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=3[CH3:41])[CH2:20][CH2:21][CH:22]2[C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH2:17]1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[OH-].[Na+]>ClCCl>[CH2:9]([N:16]1[CH2:24][C:23]2([C:25]([O:27][CH3:28])=[O:26])[C:18](=[C:19]([C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=3[CH3:41])[CH2:20][CH2:21][CH:22]2[C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)[CH2:17]1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 62406Trifluoromethanesulfonic acidHCID 86755050HCID 86755050, compound

Product 1

HCID 86755049HCID 86755049, compoundYield 89.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

A mixture of 3.2 cm3 of trifluoromethanesulphonic acid and of 3 cm3 of dichloromethane was added dropwise to a solution of 2.2 g of methyl (3aRS,4SR,7RS,7aRS)-2-benzyl-7-hydroxy-7-(2-methylphenyl)-4-phenyloctahydroisoindole-3a-carboxylate in 20 cm3 of dichloromethane maintained at a temperature in the region of 0° C. The reaction mixture was stirred for thirty minutes at a temperature in the region of 0° C. and twenty hours at a temperature in the region of 20° C. and then cooled to a temperature in the region of 0° C. The pH was then brought to 8 by addition of a normal aqueous sodium hydroxide solution. The aqueous phase was separated by settling and extracted with three times 50 cm3 of dichloromethane. The organic phases were combined, washed with three times 100 cm3 of distilled water and 100 cm3 of a saturated aqueous sodium chloride solution, dried over magnesium sulphate and concentrated under reduced pressure. 1.9 g of methyl (3aRS,4SR)-2-benzyl-7-(2-methylphenyl)-4-phenyl-1,3,3a,4,5,6-hexahydroisoindole-3a-carboxylate were thus obtained in the form of an oil, and used in the subsequent syntheses, the characteristics of which were as follows:

Workup

  1. temperaturecooled to a temperature in the region of 0° C
  2. customThe aqueous phase was separated
  3. extractionextracted with three times 50 cm3 of dichloromethane
  4. washwashed with three times 100 cm3 of distilled water and 100 cm3 of a saturated aqueous sodium chloride solution
  5. dry with materialdried over magnesium sulphate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-480c44ff40df409199fd50f7ff755ad8
Source dataset
uspto-grants-2001_04
Patent number
US06218406B1

Reaction notes

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