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Potassium Carbonate → (3aR,7aR)-Octahydro-2-(1-imino-2-(2-methoxyphenyl)ethyl)-7,7-diphenyl-4H-isoindol-4-one

HRID 1029957
Notes
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Reaction equation

HRID 1029957 reaction equation
C([O+](CC)CC)C.[CH3:8][O:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[CH2:16][C:17]([NH2:19])=O.Cl.[C:21]1([C:27]2([C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=3)[C@H:35]3[C@H:31]([CH2:32][NH:33][CH2:34]3)[C:30](=[O:36])[CH2:29][CH2:28]2)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C(=O)([O-])[O-].[K+].[K+]>ClCCl.C(N(CC)CC)C>[NH:19]=[C:17]([N:33]1[CH2:32][C@H:31]2[C@H:35]([C:27]([C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=3)([C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=3)[CH2:28][CH2:29][C:30]2=[O:36])[CH2:34]1)[CH2:16][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=1[O:9][CH3:8]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 806622-(2-Methoxyphenyl)acetamideHCID 165095TriethyloxoniumHCID 22843247(3aR,7aR)-7,7-diphenyl-4-perhydroisoindolone hydrochloride

Product 1

HCID 107686(3aR,7aR)-Octahydro-2-(1-imino-2-(2-methoxyphenyl)ethyl)-7,7-diphenyl-4H-isoindol-4-oneYield 29%

Reagents, catalysts & solvents

2
HCID 6344DichloromethaneSolvent2×HCID 8471TriethylamineSolvent

Procedure

Triethyloxonium tetrafluoborate (8.4 g) is added to a stirred suspension of 2-(2-methoxyphenyl)acetamide (6.6 g) in anhydrous dichloromethane (20 cc). Stirring of the reaction mixture is continued for 20 hours at ambient temperature. The mixture is cooled to +5° C. and a solution of (3aR,7aR)-7,7-diphenyl-4-perhydroisoindolone hydrochloride (9.8 g) and triethylamine (10.4 cc) in dichloromethane (60 cc) is then added. After the temperature has returned to ambient temperature, the reaction mixture is refluxed for 4 hours. It is then treated, after the temperature has returned to ambient temperature, with a 10% aqueous potassium carbonate solution (40 cc); the organic phase is washed with distilled water (20 cc), dried over magnesium sulphate and concentrated to dryness under reduced pressure (2.7 kPa). The residue is crystallized from acetonitrile (20 cc); the crystals obtained are drained, washed with acetonitrile (5 cc) and with isopropyl ether (10 cc) and dried. The crystals are recrystallized from acetonitrile (45 cc); the crystals obtained are drained and dried. (3aR,7aR)-2-[1-imino-2-(2-methoxyphenyl)ethyl]-7,7-diphenyl-4-perhydroisoindolone (3.8 g) melting at 191° C. is obtained. [α]D20 =-255° (c=1, methanol).

Workup

  1. temperatureThe mixture is cooled to +5° C.
  2. customhas returned to ambient temperature
  3. temperaturethe reaction mixture is refluxed for 4 hours
  4. additionIt is then treated
  5. washthe organic phase is washed with distilled water (20 cc)
  6. dry with materialdried over magnesium sulphate
  7. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)
  8. customThe residue is crystallized from acetonitrile (20 cc)
  9. customthe crystals obtained
  10. washwashed with acetonitrile (5 cc) and with isopropyl ether (10 cc)
  11. customdried
  12. customThe crystals are recrystallized from acetonitrile (45 cc)
  13. customthe crystals obtained
  14. customdried

Sources & evidence

ORD record
ord-74c5c012df1c4d46b364543d84d59e5b
Source dataset
uspto-grants-1992_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05102667

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes