Methanol → 4,10-Dihydro-5H-pyrrolo[1,2-a]thieno[3,2-e][1,4]diazepine

HRID 976366Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 976366
O=[C:2]1[NH:8][C:7]2=[CH:9][CH2:10][S:11][C:6]2=[CH:5][N:4]2[CH:12]=[CH:13][CH:14]=[C:3]12.B.CSC.CO>O1CCCC1>[S:11]1[C:6]2[CH2:5][N:4]3[CH:12]=[CH:13][CH:14]=[C:3]3[CH2:2][NH:8][C:7]=2[CH:9]=[CH:10]1

Komponenten

5

Edukt 3

HCID 887MethanolHCID 12423031(Dimethyl sulfide)trihydroboronHCID 218371505-Oxo-4,5-dihydropyrrolo[1,2-a]thieno[3,2-e][1,4]diazepine

Produkt 1

HCID 218369694,10-Dihydro-5H-pyrrolo[1,2-a]thieno[3,2-e][1,4]diazepine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a suspension of 7.0 g of 5-oxo-4,5-dihydro-pyrrolo[1,2-a]thieno[3,2-e][1,4]diazepine in 25 ml of anhydrous tetrahydrofuran is added 9 ml of 10M borane-dimethylsulfide in tetrahydrofuran. The mixture is refluxed for 6 hours. The solution is cooled to room temperature and 25 ml of methanol added dropwise. The volatiles are removed under vacuum. To the residue is added 100 ml of 2N NaOH. The mixture is refluxed 5 hours and filtered. The solid is extracted with dichloromethane and the extract is washed with 2N citric acid, water and dried (Na2SO4). The solvent is removed to give a solid.

Aufarbeitung

  1. temperatureThe mixture is refluxed for 6 hours
  2. customThe volatiles are removed under vacuum
  3. additionTo the residue is added 100 ml of 2N NaOH
  4. temperatureThe mixture is refluxed 5 hours
  5. filtrationfiltered
  6. extractionThe solid is extracted with dichloromethane
  7. washthe extract is washed with 2N citric acid, water
  8. dry with materialdried (Na2SO4)
  9. customThe solvent is removed
  10. customto give a solid

Quellen und Nachweise

ORD-Eintrag
ord-5316a6e91ce14745a80412b42c655ea3
Quelldatensatz
uspto-grants-1997_03
Patentnummer
US05612334

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