Sodium Carbonate → HCID 86755061, compound

HRID 849610Notes

Reaction equation

HRID 849610 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5](B(O)O)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Na+].[Na+].[CH3:17][O:18][C:19]([C:21]12[CH:29]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=3[O:36][CH3:37])[CH2:28][CH:27]=[C:26](I)[CH:25]1[CH2:24][N:23]([CH2:39][C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)[CH2:22]2)=[O:20]>CO.C1(C)C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:17][O:18][C:19]([C:21]12[CH:29]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=3[O:36][CH3:37])[CH2:28][CH:27]=[C:26]([C:5]3[CH:6]=[CH:7][C:2]([CH3:1])=[CH:3][CH:4]=3)[CH:25]1[CH2:24][N:23]([CH2:39][C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)[CH2:22]2)=[O:20]

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 79799Tolylboronic acidHCID 86755062HCID 86755062, compound

Product 1

HCID 86755061HCID 86755061, compoundYield 95%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 887MethanolSolventHCID 1140TolueneSolvent

Procedure

A solution of 0.41 g (2.99 mmol) of 4-methylphenylboronic acid in 13 cm3 of methanol and 30 cm3 of a 2N aqueous sodium carbonate solution were successively added to a solution of 1.37 g (2.7 mmol) of methyl(3aRS,4SR,7aRS)-2-benzyl-7-iodo-4-(2-methoxyphenyl)-2,3,3a,4,5,7a-hexahydro-1H-isoindole-3a-carboxylate and of 0.15 g (0.13 mmol) of tetrakis(triphenylphosphine)palladium in 30 cm3 of toluene and then the mixture was brought to reflux for two hours. After returning to a temperature in the region of 20° C., the reaction mixture was extracted with 100 cm3 of ethyl acetate, washed with two times 50 cm3 of distilled water, dried over magnesium sulphate and then concentrated under reduced pressure. The brown residue obtained was purified by flash chromatography on silica gel (230-400 mesh), elution being carried out with a cyclohexane/ethyl acetate (95/05 by volume) mixture. 1.2 g (93%) of methyl(3aRS,4SR,7aRS)-2-benzyl-4-(2-methoxyphenyl)-7-(4-methylphenyl)-2,3,3a,4,5,7a-hexahydro-1H-isoindole-3a-carboxylate were thus obtained in the form of a yellow oil, the characteristics of which were as follows:

Workup

  1. temperatureto reflux for two hours
  2. customAfter returning to a temperature in the region of 20° C.
  3. extractionthe reaction mixture was extracted with 100 cm3 of ethyl acetate
  4. washwashed with two times 50 cm3 of distilled water
  5. dry with materialdried over magnesium sulphate
  6. concentrationconcentrated under reduced pressure
  7. customThe brown residue obtained
  8. customwas purified by flash chromatography on silica gel (230-400 mesh), elution

Sources & evidence

ORD record
ord-d6c02dd7dbcd4f00afccf689eefaa035
Source dataset
uspto-grants-2000_01
Patent number
US06013662

Reaction notes

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