Magnesium monoxide → 2-Oxa-4-azatetracyclo[6.3.1.16,10.01,5]tridecan-3-one

HRID 2092024

Reaktionsgleichung

Reaktionsgleichung von HRID 2092024
[C:1](=[O:14])([O:3][C:4]12[CH2:13][CH:8]3[CH2:9][CH:10]([CH2:12][CH:6]([CH2:7]3)[CH2:5]1)[CH2:11]2)[NH2:2].IC1C=CC=C(CC([O-])=O)C=1CC([O-])=O.[O-2].[Mg+2]>ClCCl.CC(O)=O.CC(O)=O.CC(O)=O.CC(O)=O.[Rh].[Rh]>[C:4]123[CH2:5][CH:6]4[CH2:12][CH:10]([CH2:9][CH:8]([CH2:7]4)[CH:13]1[NH:2][C:1](=[O:14])[O:3]2)[CH2:11]3

Komponenten

6

Edukt 3

HCID 6850729Magnesium monoxideHCID 124376461-Adamantyl carbamateHCID 219456882-[2-(Carboxylatomethyl)-3-iodophenyl]acetate

Produkt 1

HCID 28074452-Oxa-4-azatetracyclo[6.3.1.16,10.01,5]tridecan-3-oneAusbeute 77 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 423677Acetic acid, rhodium salt (4:2)KatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Tricyclo[3.3.1.13,7]dec-1-yl carbamate (100 mg, 0.512 mmol), iodobenzenediacetate (220 mg, 0.683 mmol), magnesium oxide (50 mg, 1.24 mmol) and rhodium (II) acetate dimer (22 mg, 0.050 mmol) were stirred in dichloromethane (3 mL) at 50° C. for 5 hours. After completion of the reaction, the reaction solution was filtered, and the solid was washed with chloroform and the filtrate was evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate=10/1→2/1) to give the desired product (77% yield).

Aufarbeitung

  1. customAfter completion of the reaction
  2. filtrationthe reaction solution was filtered
  3. washthe solid was washed with chloroform
  4. customthe filtrate was evaporated under reduced pressure
  5. customThe resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate=10/1→2/1)

Quellen und Nachweise

ORD-Eintrag
ord-d4ce184fdb4f48e6b71ded0bd1b8f1ab
Quelldatensatz
uspto-grants-2013_05
Patentnummer
US08440666B2

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