Borane;tetrahydrofuran → HCID 69303662, Verbindung

HRID 1793685Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1793685
B1(C)OC(C2C=CC=CC=2)(C2C=CC=CC=2)[C@H]2N1CCC2.B.C1COCC1.[Cl:28][CH2:29][C:30]([C:32]1[CH:33]=[C:34]2[C:38](=[C:39]([Cl:41])[CH:40]=1)[NH:37][C:36](=[O:42])[CH2:35]2)=[O:31]>C1COCC1>[Cl:41][C:39]1[C:38]2[C:34](=[CH:35][C:36](=[O:42])[N:37]=2)[CH:33]=[C:32]([C@H:30]([OH:31])[CH2:29][Cl:28])[CH:40]=1

Komponenten

5

Edukt 3

HCID 2723981Borane;tetrahydrofuran2×HCID 2734713(3aS)-1-methyl-3,3-diphenyl-hexahydropyrrolo(1,2-c)(1,3,2)oxazaboroleHCID 220211197-Chloro-5-(2-chloroacetyl)-1,3-dihydro-2H-indol-2-one

Produkt 1

HCID 69303662HCID 69303662, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of (S)-Methyl-CBS-oxazaborolidine (1M in toluene, 0.745 mL, 0.745 mmol) and BH3-THF (8 mL, 8 mmol) is added at the same time a solution of BH3-THF (19 mL, 19 mmol) and a solution of the 5-Chloroacetyl-7-chlorooxindole (37.98 mmol) in 19 mL of THF. Both solutions are added dropwise over 30 minutes. The solution is stirred for 1 hour and quenched with the slow addition of methanol (50 mL). The solution is concentrated and the residue chromatographed over a short silica gel column (1:1 hexane/ethyl acetate).

Aufarbeitung

  1. additionBoth solutions are added dropwise over 30 minutes
  2. customquenched with the slow addition of methanol (50 mL)
  3. concentrationThe solution is concentrated
  4. customthe residue chromatographed over a short silica gel column (1:1 hexane/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-388628bce0db46959552074fa18b9c22
Quelldatensatz
uspto-grants-2006_07
Patentnummer
US07081454B2

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