Triethylamine → (3aR,4S,7aR)-7,7-diphenyl-2-[1-imino-2-(2-methoxyphenyl)ethyl]-4-perhydroisoindolol

HRID 1721220노트

반응식

HRID 1721220 반응식
F[B-](F)(F)F.[CH3:6][O:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[CH2:14][C:15](=[NH:19])OCC.C(N(CC)CC)C.[C:27]1([C:33]2([C:43]3[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=3)[C@H:41]3[C@H:37]([CH2:38][NH:39][CH2:40]3)[C@@H:36]([OH:42])[CH2:35][CH2:34]2)[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.C(=O)([O-])[O-].[K+].[K+]>ClCCl>[C:43]1([C:33]2([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[C@H:41]3[C@H:37]([CH2:38][N:39]([C:15](=[NH:19])[CH2:14][C:9]4[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=4[O:7][CH3:6])[CH2:40]3)[C@@H:36]([OH:42])[CH2:35][CH2:34]2)[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=1

참가 물질

6

반응물 4

HCID 8471TriethylamineHCID 11430Potassium CarbonateHCID 22856102(3aR,4S,7aR)-7,7-diphenyl-4-perhydroisoindololHCID 86749006Ethyl (2-methoxyphenyl)acetimidate tetrafluoroborate

생성물 1

HCID 22856098(3aR,4S,7aR)-7,7-diphenyl-2-[1-imino-2-(2-methoxyphenyl)ethyl]-4-perhydroisoindolol수율 57%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

A solution of 1.56 g of ethyl (2-methoxyphenyl)acetimidate tetrafluoroborate and 0.96 cm3 of triethylamine in 20 cm3 of dry dichloromethane is added to a solution of 2 g of (3aR,4S,7aR)-7,7-diphenyl-4-perhydroisoindolol in 30 cm3 of dry dichloromethane, and then the reaction mixture is refluxed for 2 hours. 10 cm3 of a 10% aqueous solution of potassium carbonate are then added, decanted and then the organic phase is washed with 20 cm3 of water, dried over magnesium sulphate, filtered and concentrated to dryness under reduced pressure (2.7 kPa). The residue is chromatographed on an alumina column (diameter 3.6 cm, height 31 cm), eluting under a nitrogen pressure of 0.1 bar with a dichloromethane and methanol mixture (95/5 by volume) and collecting fractions of 50 cm3. Fractions 5 to 30 are pooled and concentrated to dryness under reduced pressure (2.7 kPa). The solid obtained is washed with isopropyl oxide, drained and dried. 1.4 g of (3aR,4S,7aR)-7,7-diphenyl-2-[1-imino-2-(2-methoxyphenyl)ethyl]-4-perhydroisoindolol are obtained in the form of white crystals; melting point 105° C., with decomposition.

후처리

  1. temperaturethe reaction mixture is refluxed for 2 hours
  2. customdecanted
  3. washthe organic phase is washed with 20 cm3 of water
  4. dry with materialdried over magnesium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)
  7. customThe residue is chromatographed on an alumina column (diameter 3.6 cm, height 31 cm)
  8. washeluting under a nitrogen pressure of 0.1 bar with a dichloromethane and methanol mixture (95/5 by volume)
  9. customcollecting fractions of 50 cm3
  10. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)
  11. customThe solid obtained
  12. washis washed with isopropyl oxide
  13. customdried

출처 및 근거

ORD 기록
ord-19eece2d4f694154af18e67f881b9f99
출처 데이터셋
uspto-grants-1996_04
특허 번호
US05508433

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