(3R*,4R*)-N,N-Diethyl-6-diphenylmethyl-5,5-ethylenedioxy-1-azabicyclo[2.2.2]octane-3-carboxamide → (3R*,4S*)-N,N-Diethyl-6-diphenylmethyl-5,5-ethylenedioxy-1-azabicyclo[2.2.2]octane-3-carboxamide

HRID 862118Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 862118
[CH2:1]([N:3]([CH2:31][CH3:32])[C:4]([C@@H:6]1[C@H:11]2[CH2:12][CH2:13][N:8]([CH:9]([CH:18]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[C:10]32[O:17][CH2:16][CH2:15][O:14]3)[CH2:7]1)=[O:5])[CH3:2]>C[O-].[Na+]>[CH2:31]([N:3]([CH2:1][CH3:2])[C:4]([C@@H:6]1[C@@H:11]2[CH2:12][CH2:13][N:8]([CH:9]([CH:18]([C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=3)[C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)[C:10]32[O:17][CH2:16][CH2:15][O:14]3)[CH2:7]1)=[O:5])[CH3:32]

Komponenten

3

Edukt 1

HCID 53633469(3R*,4R*)-N,N-Diethyl-6-diphenylmethyl-5,5-ethylenedioxy-1-azabicyclo[2.2.2]octane-3-carboxamide

Produkt 1

HCID 53633467(3R*,4S*)-N,N-Diethyl-6-diphenylmethyl-5,5-ethylenedioxy-1-azabicyclo[2.2.2]octane-3-carboxamideAusbeute 87 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 10942334Sodium MethoxideLösungsmittel

Versuchsvorschrift

A suspension of 21 (9.8 g, 22 mmol) in sodium methoxide (28% in MeOH; 400 g) was heated at reflux temperature for 9 hours. The resulting solution was poured on ice (300 ml) and extracted with CH2Cl2 (150 ml) three times. The combined extracts were dried over sodium sulfate (Na2SO4) and concentrated. The clude was purified by recrystallization from ethanol (EtOH) to give 22 (1:4 mixture at 6-position; 8.4 g, 19 mmol, 87%).

Aufarbeitung

  1. temperaturewas heated
  2. temperatureat reflux temperature for 9 hours
  3. additionThe resulting solution was poured on ice (300 ml)
  4. extractionextracted with CH2Cl2 (150 ml) three times
  5. dry with materialThe combined extracts were dried over sodium sulfate (Na2SO4)
  6. concentrationconcentrated
  7. customThe clude was purified by recrystallization from ethanol (EtOH)

Quellen und Nachweise

ORD-Eintrag
ord-6f9986fb4c534a89a3371528cd179af1
Quelldatensatz
uspto-grants-1998_02
Patentnummer
US05716965

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