Bromocresol Green → (3aR*,10aS*)-9-(4-Nitrobenzyl)-2,3,3a,4,9,10a-hexahydrobenzo[b]cyclopenta[e][1,4]diazepin-10(1H)-one

HRID 361563

Reaktionsgleichung

Reaktionsgleichung von HRID 361563
[N+:1]([C:4]1[CH:25]=[CH:24][C:7]([CH2:8][N:9]2[C:15](=[O:16])[CH:14]3[CH2:17][CH2:18][CH2:19][C:13]3=[N:12][C:11]3[CH:20]=[CH:21][CH:22]=[CH:23][C:10]2=3)=[CH:6][CH:5]=1)([O-:3])=[O:2].CC1C(Br)=C(O)C(Br)=CC=1C1(C2C=C(Br)C(O)=C(Br)C=2C)OS(=O)(=O)C2C=CC=CC1=2.C([BH3-])#N.[Na+].Cl.CO>CO.O.O1CCCC1>[N+:1]([C:4]1[CH:25]=[CH:24][C:7]([CH2:8][N:9]2[C:15](=[O:16])[C@H:14]3[CH2:17][CH2:18][CH2:19][C@H:13]3[NH:12][C:11]3[CH:20]=[CH:21][CH:22]=[CH:23][C:10]2=3)=[CH:6][CH:5]=1)([O-:3])=[O:2]

Komponenten

8

Edukt 4

HCID 6451Bromocresol GreenHCID 5003444Sodium cyanoborohydrideHCID 21893726Hydrochloride methanolHCID 701129649-(4-Nitrobenzyl)-2,3,9,10a-tetrahydrobenzo[b]cyclopenta[e][1,4]diazepin-10(1H)-one

Produkt 1

HCID 54563031(3aR*,10aS*)-9-(4-Nitrobenzyl)-2,3,3a,4,9,10a-hexahydrobenzo[b]cyclopenta[e][1,4]diazepin-10(1H)-oneAusbeute 70,1 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a suspension of 9-(4-nitrobenzyl)-2,3,9,10a-tetrahydrobenzo[b]cyclopenta(e][1,4]diazepin-10(1H)-one (10.2 g, 30 mmol) and bromocresol green in a mixture of methanol (100 mL)-tetrahydrofuran (THF) (30 mL) was added sodium cyanoborohydride (2.08 g, 33 mmol). To this mixture, 10% hydrogen chloride/methanol was slowly added dropwise at the same temperature until the color of the reaction mixture had ceased to change. This reaction mixture was diluted with water and extracted with 3 portions of ethyl acetate. The pooled organic layer was washed serially with water and saturated aqueous NaCl solution, dried over MgSO4, filtered, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane-ethyl acetate=2:1) and crystallized from ethyl acetate-diethyl ether to provide 7.09 g (yield 70%) of the title compound. m.p. 154°-155° C.

Aufarbeitung

  1. extractionextracted with 3 portions of ethyl acetate
  2. washThe pooled organic layer was washed serially with water and saturated aqueous NaCl solution
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (hexane-ethyl acetate=2:1)
  7. customcrystallized from ethyl acetate-diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-4d7e3e52a14943f7a283dc3c2c400228
Quelldatensatz
uspto-grants-1999_02
Patentnummer
US05866567

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