2-Methoxyphenylacetic acid → (3aRS,4RS,5RS,7aRS)-7,7-diphenyl-4-(2-methoxyphenyl)-2-(2-methoxyphenyl)-acetylperhydroisoindole-4,5-diol

HRID 1780972Notes

Reaction equation

HRID 1780972 reaction equation
Cl.[C:2]1([C:8]2([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[CH:16]3[CH:12]([CH2:13][NH:14][CH2:15]3)[C:11]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[O:24][CH3:25])([OH:17])[CH:10]([OH:26])[CH2:9]2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH3:40][O:41][C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][C:43]=1[CH2:48][C:49](O)=[O:50]>ClCCl>[C:27]1([C:8]2([C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[CH:16]3[CH:12]([CH2:13][NH:14][CH:15]3[C:49](=[O:50])[CH2:48][C:43]3[CH:44]=[CH:45][CH:46]=[CH:47][C:42]=3[O:41][CH3:40])[C:11]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[O:24][CH3:25])([OH:17])[CH:10]([OH:26])[CH2:9]2)[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

5

Reactant 3

HCID 71342-Methoxyphenylacetic acidHCID 8471TriethylamineHCID 677192977,7-Diphenyl-4-(2-methoxyphenyl)-perhydroisoindole-4,5-diol hydrochloride

Product 1

HCID 67719041(3aRS,4RS,5RS,7aRS)-7,7-diphenyl-4-(2-methoxyphenyl)-2-(2-methoxyphenyl)-acetylperhydroisoindole-4,5-diolYield 77.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 4.5 g of (3aRS,4RS,5RS,7aRS)-7,7-diphenyl-4-(2-methoxyphenyl)perhydro-4,5-isoindolediol hydrochloride in 100 cm3 of dichloromethane, cooled to 0° C., are added 4.2 cm3 of triethylamine, followed by 2.4 g of (2-methoxyphenyl)acetic acid in 50 cm3 of dichloromethane. Stirring is carried out at room temperature for 90 minutes; the reaction mixture is washed with twice 10 cm3 of water, dried over magnesium sulphate and concentrated to dryness under reduced pressure (2.7 kPa). The crystallized solid is taken up with 100 cm3 of diisopropyl ether and then filtered, washed with 50 cm3 of saturated sodium bicarbonate solution and then with 50 cm3 of diisopropyl ether. 4.35 g of (3aRS,4RS,5RS,7aRS)-7,7-diphenyl-4-(2-methoxyphenyl)-2-(2-methoxyphenyl)acetylperhydro-4,5-isoindolediol are obtained, in the form of a light beige solid melting at 278° C.

Workup

  1. washthe reaction mixture is washed with twice 10 cm3 of water
  2. dry with materialdried over magnesium sulphate
  3. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)
  4. filtrationfiltered
  5. washwashed with 50 cm3 of saturated sodium bicarbonate solution

Sources & evidence

ORD record
ord-3a7d3fcf84904af89b0162e8dcc4e243
Source dataset
uspto-grants-1997_05
Patent number
US05631279

Reaction notes

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