propyl [2-(4-diazo-3-oxobutyl)-1H-indol-3-yl]acetate → Propyl (7-oxo-6,7,8,9-tetrahydropyrido[1,2-a]indol-10-yl)acetate

HRID 476226

Reaktionsgleichung

Reaktionsgleichung von HRID 476226
[N+](=[CH:3][C:4](=[O:23])[CH2:5][CH2:6][C:7]1[NH:8][C:9]2[C:14]([C:15]=1[CH2:16][C:17]([O:19][CH2:20][CH2:21][CH3:22])=[O:18])=[CH:13][CH:12]=[CH:11][CH:10]=2)=[N-]>C([O-])(=O)CCCCCCC.[Rh+2].C([O-])(=O)CCCCCCC.C(Cl)Cl>[O:23]=[C:4]1[CH2:3][N:8]2[C:9]3[C:14]([C:15]([CH2:16][C:17]([O:19][CH2:20][CH2:21][CH3:22])=[O:18])=[C:7]2[CH2:6][CH2:5]1)=[CH:13][CH:12]=[CH:11][CH:10]=3

Komponenten

4

Edukt 1

HCID 86655415propyl [2-(4-diazo-3-oxobutyl)-1H-indol-3-yl]acetate

Produkt 1

HCID 58399159Propyl (7-oxo-6,7,8,9-tetrahydropyrido[1,2-a]indol-10-yl)acetateAusbeute 64 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 10178397Rhodium(II) octanoateKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Rhodium (II) octanoate dimmer (0.1 equiv.) was added to a CH2Cl2 solution (0.02 M) of propyl [2-(4-diazo-3-oxobutyl)-1H-indol-3-yl]acetate from Step 4. The reaction mixture was stirred overnight at rt and then concentrated. The residue was purified by column chromatography on silica gel using automatized gradiant pump system CombiFlashRF (Teledyne ISCO) eluting with EtOAc/Hexane (2:98 to 10:90) to give the title compound (64%) as a yellow solid.

Aufarbeitung

  1. concentrationconcentrated
  2. customThe residue was purified by column chromatography on silica gel using automatized gradiant pump system CombiFlashRF (Teledyne ISCO)
  3. washeluting with EtOAc/Hexane (2:98 to 10:90)

Quellen und Nachweise

ORD-Eintrag
ord-a20c9f11ee5d46ecafec9752809a5003
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08637671B2

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