Water → 6,7-dihydro-5H-pyrrolo[1,2-a][1,5]benzodiazepine

HRID 55208

Reaktionsgleichung

Reaktionsgleichung von HRID 55208
[CH:1]1[C:11]2[N:10]3[CH:12]=[CH:13][CH:14]=[C:9]3[CH2:8][C:7](=O)[NH:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.B#B.CSC.O.[OH-].[Na+]>O1CCCC1>[CH:1]1[C:11]2[N:10]3[CH:12]=[CH:13][CH:14]=[C:9]3[CH2:8][CH2:7][NH:6][C:5]=2[CH:4]=[CH:3][CH:2]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 123593406,7-dihydro-5H-pyrrolo[1,2-a][1,5]benzodiazepin-6-oneHCID 22038413Diborane dimethylsulfide

Produkt 1

HCID 123593416,7-dihydro-5H-pyrrolo[1,2-a][1,5]benzodiazepineAusbeute 99,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a solution of 0.070 g of 6,7-dihydro-5H-pyrrolo[1,2-a][1,5]benzodiazepin-6-one in 2 ml of tetrahydrofuran is added 0.45 ml of a 2.0M solution of diborane-dimethylsulfide in tetrahydrofuran. The mixture is refluxed for 3 hours, poured into water and make basic with 2N NaOH. The tetrahydrofuran is removed under vacuum and the residual aqueous mixture extracted with diethyl ether. The extract is washed with brine, dried (Na2SO4) and the solvent removed to give 0.065 g of a colorless oil; one spot by thin layer chromatography (silica gel) with ethyl acetate-hexane (1:2) as solvent (Rf 0.81).

Aufarbeitung

  1. temperatureThe mixture is refluxed for 3 hours
  2. customThe tetrahydrofuran is removed under vacuum
  3. extractionthe residual aqueous mixture extracted with diethyl ether
  4. washThe extract is washed with brine
  5. dry with materialdried (Na2SO4)
  6. customthe solvent removed

Quellen und Nachweise

ORD-Eintrag
ord-37422a41c500449095126818b5dce1c8
Quelldatensatz
uspto-grants-1997_04
Patentnummer
US05624923

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