Ammonia → (3aRS,7aRS)-2-[1-Imino-2-(2-methoxyphenyl)ethyl]-7,7-diphenylperhydro-4-isoindolone

HRID 1196272Notes

Reaction equation

HRID 1196272 reaction equation
[NH3:1].F[B-](F)(F)F.C(O[C:10](=[N+:20]1[CH2:28][CH:27]2[CH:22]([C:23]([C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[CH2:24][CH2:25][C:26]2=[O:29])[CH2:21]1)[CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[O:18][CH3:19])C.C(=O)([O-])[O-].[K+].[K+]>ClCCl>[NH:1]=[C:10]([N:20]1[CH2:28][CH:27]2[CH:22]([C:23]([C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)([C:30]3[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=3)[CH2:24][CH2:25][C:26]2=[O:29])[CH2:21]1)[CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[O:18][CH3:19]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 11430Potassium CarbonateHCID 86745794(3aRS,7aRS)-2-[1-Ethoxy-2-(2-methoxyphenyl)ethylidene]-4-oxo-7,7-diphenylperhydroisoindolium tetrafluoroborate

Product 1

HCID 3505088(3aRS,7aRS)-2-[1-Imino-2-(2-methoxyphenyl)ethyl]-7,7-diphenylperhydro-4-isoindolone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A 5.4N ethanolic solution (1.3 cc) of ammonia is added to a stirred suspension, cooled to -10° C., of (3aRS,7aRS)-2-[1-ethoxy-2-(2-methoxyphenyl)ethylidene]-4-oxo-7,7-diphenylperhydroisoindolium tetrafluoroborate (5.7 g) in anhydrous dichloromethane (15 cc). The reaction mixture is then allowed to return to room temperature and stirring is continued for 20 hours. The reaction mixture is diluted with dichloromethane (20 cc) and treated with 10% strength aqueous potassium carbonate solution (20 cc). The precipitate present is removed by filtration and the organic phase is then washed with distilled water (25 cc) and with saturated aqueous sodium chloride solution (25 cc), dried over magnesium sulphate and concentrated to dryness under reduced pressure (2.7 kPa). The residue is crystallized in acetonitrile (10 cc). The crystals obtained are drained, washed with acetonitrile (10 cc) and dried. and dried. (3aRS,7aRS)-2-[1-Imino-2-(2-methoxyphenyl)ethyl]-7,7-diphenylperhydro-4-isoindolone (1 g), m.p. above 260° C. is obtained.

Workup

  1. customto return to room temperature
  2. customThe precipitate present is removed by filtration
  3. washthe organic phase is then washed with distilled water (25 cc) and with saturated aqueous sodium chloride solution (25 cc)
  4. dry with materialdried over magnesium sulphate
  5. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)
  6. customThe residue is crystallized in acetonitrile (10 cc)
  7. customThe crystals obtained
  8. washwashed with acetonitrile (10 cc)
  9. customdried
  10. customand dried

Sources & evidence

ORD record
ord-566b50421afe49a99d848499a3b2eb47
Source dataset
uspto-grants-1992_05
Patent number
US05112988

Reaction notes

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