6-methoxy-1-methylene-3,4-dihydro-1H-isoquinoline-2-carboxylic acid benzyl ester → 7-Methoxy-2-oxo-1,2,4,5-tetrahydrobenzo[d]azepine-3-carboxylic acid benzyl ester

HRID 6763Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 6763
[CH2:1]([O:8][C:9]([N:11]1[CH2:20][CH2:19][C:18]2[C:13](=[CH:14][CH:15]=[C:16]([O:21][CH3:22])[CH:17]=2)[C:12]1=[CH2:23])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])(=[O:26])C.C([O-])(=O)C.C([O-])(=O)C.C([O-])(=O)C.[Pb+4]>C(O)(=O)C>[CH2:1]([O:8][C:9]([N:11]1[CH2:20][CH2:19][C:18]2[CH:17]=[C:16]([O:21][CH3:22])[CH:15]=[CH:14][C:13]=2[CH2:23][C:12]1=[O:26])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

4

Edukt 2

HCID 138591896-methoxy-1-methylene-3,4-dihydro-1H-isoquinoline-2-carboxylic acid benzyl esterHCID 178418268HCID 178418268, Verbindung

Produkt 1

HCID 235442487-Methoxy-2-oxo-1,2,4,5-tetrahydrobenzo[d]azepine-3-carboxylic acid benzyl esterAusbeute 28,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

To a solution of 6-methoxy-1-methylene-3,4-dihydro-1H-isoquinoline-2-carboxylic acid benzyl ester (0.66 g) in 20 mL of glacial acetic acid was added lead tetraacetate (1 g). The reaction was stirred overnight, then quenched by the addition of 2 mL of glycerol. The volatile material was evaporated and the resulting residue was partitioned between 50 mL of saturated sodium chloride and 50 mL of dichloromethane. The aqueous phase was re-extracted with 50 mL more dichloromethane and the combined extracts were dried over sodium sulfate. The volatile material was evaporated and chromatography (20% ethyl acetate in hexanes) yielded 0.20 g of 7-methoxy-2-oxo-1,2,4,5-tetrahydrobenzo[d]azepine-3-carboxylic acid benzyl ester.

Aufarbeitung

  1. customquenched by the addition of 2 mL of glycerol
  2. customThe volatile material was evaporated
  3. customthe resulting residue was partitioned between 50 mL of saturated sodium chloride and 50 mL of dichloromethane
  4. extractionThe aqueous phase was re-extracted with 50 mL more dichloromethane
  5. dry with materialthe combined extracts were dried over sodium sulfate
  6. customThe volatile material was evaporated

Quellen und Nachweise

ORD-Eintrag
ord-20d207dccb154960a6a6d8d38ffea590
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07084154B2

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