Dimethyl Carbonate → Methyl 1-benzyl-2-oxoazepane-3-carboxylate

HRID 467470Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 467470
[CH2:1]([N:8]1[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][C:9]1=[O:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Li+].CC([N-]C(C)C)C.[C:24](=O)([O:27]C)[O:25][CH3:26]>CCOCC>[CH2:1]([N:8]1[CH2:14][CH2:13][CH2:12][CH2:11][CH:10]([C:24]([O:25][CH3:26])=[O:27])[C:9]1=[O:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 12021Dimethyl CarbonateHCID 14910681-Benzylazepan-2-oneHCID 2724682Lithium diisopropylamide

Produkt 1

HCID 21902024Methyl 1-benzyl-2-oxoazepane-3-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

A cooled (−78° C.) solution of 1-2 (2 g, 9.84 mmol) in Et2O (50 ml) was treated with LDA (9.84 ml, 19.68 mmol) and stirred for 1 h. The mixture was treated with dimethyl carbonate (1.658 ml, 19.68 mmol), warmed to RT and stirred overnight. The mixture was quenched with 1N HCl and extracted twice with EtOAc. The organic phase was dried over Na2SO4, filtered and concentrated. The crude material was purified by gradient elution on silica gel (0 to 60% EtOAc in Hex) to yield a 1:1 mixture of 1-3 and starting material as a tan oil. Data for 1-3: LRMS m/z (M+H): 262.1.

Aufarbeitung

  1. stirringstirred overnight
  2. customThe mixture was quenched with 1N HCl
  3. extractionextracted twice with EtOAc
  4. dry with materialThe organic phase was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude material was purified by gradient elution on silica gel (0 to 60% EtOAc in Hex)
  8. customto yield
  9. additiona 1:1 mixture of 1-3

Quellen und Nachweise

ORD-Eintrag
ord-41e3d9850e4744a88b246d49586fed64
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08623863B2

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