(6R,7R)-2,2-dimethyl-7-phthalimido-1-aza-3-oxabicyclo[4.2.0]octan-8-one → (6R,7R)-7-amino-2,2-dimethyl-1-aza-3-oxabicyclo[4.2.0]octan-8-one

HRID 1719303Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1719303
CNN(CCC)NC.[CH3:9][C:10]1([CH3:30])[O:17][CH2:16][CH2:15][C@H:14]2[N:11]1[C:12](=[O:29])[C@@H:13]2[N:18]1C(=O)C2=CC=CC=C2C1=O>CO.ClCCl>[NH2:18][C@H:13]1[C:12](=[O:29])[N:11]2[C@@H:14]1[CH2:15][CH2:16][O:17][C:10]2([CH3:30])[CH3:9]

Komponenten

5

Edukt 2

HCID 53799173(6R,7R)-2,2-dimethyl-7-phthalimido-1-aza-3-oxabicyclo[4.2.0]octan-8-oneHCID 56982963N,N-dimethylaminopropylamine

Produkt 1

HCID 12804734(6R,7R)-7-amino-2,2-dimethyl-1-aza-3-oxabicyclo[4.2.0]octan-8-oneAusbeute 59,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

N,N-Dimethylaminopropylamine (91 μl) was added to a solution of (6R,7R)-2,2-dimethyl-7-phthalimido-1-aza-3-oxabicyclo[4.2.0]octan-8-one (80 mg) in a mixture of methanol (1.4 ml) and dichloromethane (0.7 ml) at 0° C. under a nitrogen atmosphere. The solution was stirred at the same temperature for two hours and left at ambient temperature for 24 hours. The mixture was evaporated and the residue was chromatographed on silica gel (1.5 g; eluting with 3 to 5% methanol in dichloromethane) to give 27 mg (59.5%) of (6R,7R)-7-amino-2,2-dimethyl-1-aza-3-oxabicyclo[4.2.0]octan-8-one: IR (CH2Cl2): 3100-3600 (broad) and 1735 cm-1 ; NMR (CDCl3) δ: 1.41 (s, 3H), 1.72 (s, 3H), 1.5-2.1 (m, 4H), 3.34 (ddd, J=2, 5 and 10 Hz, 1H), and 3.7-3.9 (m, 3H).

Aufarbeitung

  1. waitleft at ambient temperature for 24 hours
  2. customThe mixture was evaporated
  3. customthe residue was chromatographed on silica gel (1.5 g; eluting with 3 to 5% methanol in dichloromethane)

Quellen und Nachweise

ORD-Eintrag
ord-92732aeb9acb4f2e8effb0e3a62e6cb1
Quelldatensatz
uspto-grants-1985_09
Patentnummer
US04539152

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