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Hydrogen Bromide → 9-(8-azabicyclo[3.2.1]octan-3-ylidene)-N,N-diethylxanthene-3-carboxamide

HRID 425277
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 425277
C(OC([N:6]1[CH:11]2[CH2:12][CH2:13][CH:7]1[CH2:8][C:9](=[C:14]1[C:27]3[CH:26]=[CH:25][C:24]([C:28](=[O:34])[N:29]([CH2:32][CH3:33])[CH2:30][CH3:31])=[CH:23][C:22]=3[O:21][C:20]3[C:15]1=[CH:16][CH:17]=[CH:18][CH:19]=3)[CH2:10]2)=O)C.Br>C(O)(=O)C>[CH2:32]([N:29]([CH2:30][CH3:31])[C:28]([C:24]1[CH:25]=[CH:26][C:27]2[C:14](=[C:9]3[CH2:10][CH:11]4[NH:6][CH:7]([CH2:13][CH2:12]4)[CH2:8]3)[C:15]3[C:20]([O:21][C:22]=2[CH:23]=1)=[CH:19][CH:18]=[CH:17][CH:16]=3)=[O:34])[CH3:33]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

4

Edukt 2

HCID 260Hydrogen BromideHCID 578392423-(3-Diethylcarbamoyl-xanthen-9-ylidene)-8-aza-bicyclo[3.2.1]octane-8-carboxylic acid ethyl ester

Produkt 1

HCID 469181419-(8-azabicyclo[3.2.1]octan-3-ylidene)-N,N-diethylxanthene-3-carboxamideAusbeute 56,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel2×

Versuchsvorschrift

A sample of compound 8a (16.0 g, 34.8 mmol) was dissolved in 35 mL acetic acid and 100 mL of 30% HBr in acetic acid was added to the reaction under Argon before heating on a steam bath for 1 h. The reaction was cooled, added to ice cold NaOH and extracted with CH2Cl2. The combined organics were washed with brine and dried over potassium carbonate. Evaporation of the solvent provided 12 g of crude Compound 10a, which was purified by column chromatography with 7% 2 N NH3 in methanol/93% CH2Cl2. to give 7.66 g (19.7 mmol) of Compound 10a. MS m/z=389.3 (M+1); 1H NMR 300 MHz (CDCl3) δ 1.1-1.4 (m, 6H), 1.7 (m, 2H), 2.7-3.0 (m, 4H), 3.4 (br s, 4H), 3.5-3.7 (m, 4H), 7.0-7.3 (m, 7H).

Aufarbeitung

  1. temperaturebefore heating on a steam bath for 1 h
  2. temperatureThe reaction was cooled
  3. additionadded to ice cold NaOH
  4. extractionextracted with CH2Cl2
  5. washThe combined organics were washed with brine
  6. dry with materialdried over potassium carbonate
  7. customEvaporation of the solvent
  8. customprovided 12 g of crude Compound 10a, which
  9. customwas purified by column chromatography with 7% 2 N NH3 in methanol/93% CH2Cl2

Quellen und Nachweise

ORD-Eintrag
ord-857dc2e5d45b497d99cbd42d57f0b177
Quelldatensatz
uspto-grants-2012_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08106207B2

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