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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
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HRID 1029957 반응식
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]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 6344Dichloromethane용매2회
HCID 8471Triethylamine용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-74c5c012df1c4d46b364543d84d59e5b
출처 데이터셋
uspto-grants-1992_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05102667

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