Triethylamine → (3aRS,7aRS)-7,7-diphenyl-2-[(2,5-dimethoxyphenyl)acetyl]-4-perhydroisoindolone

HRID 1029894

Reaction equation

HRID 1029894 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([O:9][CH3:10])=[CH:5][C:4]=1[CH2:11][C:12]([OH:14])=O.Cl.[C:16]1([C:22]2([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[CH:30]3[CH:26]([CH2:27][NH:28][CH2:29]3)[C:25](=[O:31])[CH2:24][CH2:23]2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(N(CC)CC)C>ClCCl>[C:32]1([C:22]2([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH:30]3[CH:26]([CH2:27][N:28]([C:12](=[O:14])[CH2:11][C:4]4[CH:5]=[C:6]([O:9][CH3:10])[CH:7]=[CH:8][C:3]=4[O:2][CH3:1])[CH2:29]3)[C:25](=[O:31])[CH2:24][CH2:23]2)[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 744692,5-Dimethoxyphenylacetic acidHCID 212645437,7-Diphenylhexahydro-1H-isoindol-4(2H)-one hydrochloride

Product 1

HCID 67915969(3aRS,7aRS)-7,7-diphenyl-2-[(2,5-dimethoxyphenyl)acetyl]-4-perhydroisoindoloneYield 46.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

N,N'-Carbonyldiimidazole (1.14 g) is added to a solution of 2,5-dimethoxyphenylacetic acid (1.34 g) in dry dichloromethane (30 cc), cooled to +5° C. The mixture is stirred for 30 minutes at +5° C. and a solution of (3aRS,7aRS)-7,7-diphenyl-4-perhydroisoindolone hydrochloride (2.28 g) and triethylamine (1.96 cc) in dichloromethane (20 cc) is then added. The reaction mixture is stirred at 20° C. for 16 hours, then washed with water (2×200 cc), dried over magnesium sulphate and filtered and the filtrate is concentrated to dryness under reduced pressure (2.7 kPa). The meringue obtained is crystallized from a mixture of acetonitrile (20 cc) and isopropyl ether (80 cc). The crystals are drained, washed with isopropyl ether (25 cc) and dried. (3aRS,7aRS)-7,7-diphenyl-2-[(2,5-dimethoxyphenyl)acetyl]-4-perhydroisoindolone (1.5 g) is obtained in the form of white crystals melting at 209° C.

Workup

  1. temperaturecooled to +5° C
  2. stirringThe reaction mixture is stirred at 20° C. for 16 hours
  3. washwashed with water (2×200 cc)
  4. dry with materialdried over magnesium sulphate
  5. filtrationfiltered
  6. concentrationthe filtrate is concentrated to dryness under reduced pressure (2.7 kPa)
  7. customThe meringue obtained
  8. customis crystallized from a mixture of acetonitrile (20 cc) and isopropyl ether (80 cc)
  9. washwashed with isopropyl ether (25 cc)
  10. customdried

Sources & evidence

ORD record
ord-039c8ca8f4f64ce991025dced8b95fb9
Source dataset
uspto-grants-1992_04
Patent number
US05102667

Linked notes

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