Triethylamine → N-[8-Methyl-8-azabicyclo[3.2.1]oct-3-yl]-[7-(tert-butoxy-carbonyl)-7-azaspiro[3.5]non-2-yl]acetamide

HRID 1059357Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1059357
[C:1]([O:5][C:6]([N:8]1[CH2:20][CH2:19][C:11]2([CH2:14][CH:13]([CH2:15][C:16](O)=[O:17])[CH2:12]2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.ClC(OCC)=O.Cl.Cl.[NH2:36][CH:37]1[CH2:43][CH:42]2[N:44]([CH3:45])[CH:39]([CH2:40][CH2:41]2)[CH2:38]1>ClCCl.O>[CH3:45][N:44]1[CH:39]2[CH2:40][CH2:41][CH:42]1[CH2:43][CH:37]([NH:36][C:16](=[O:17])[CH2:15][CH:13]1[CH2:12][C:11]3([CH2:10][CH2:9][N:8]([C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[CH2:20][CH2:19]3)[CH2:14]1)[CH2:38]2

Komponenten

7

Edukt 4

HCID 8471Triethylamine2×HCID 10928Ethyl chloroformateHCID 27759288-methyl-8-azabicyclo[3.2.1]octan-3-amine DihydrochlorideHCID 186705702-(7-((Tert-butoxy)carbonyl)-7-azaspiro(3.5)nonan-2-yl)acetic acid

Produkt 1

HCID 18670154N-[8-Methyl-8-azabicyclo[3.2.1]oct-3-yl]-[7-(tert-butoxy-carbonyl)-7-azaspiro[3.5]non-2-yl]acetamideAusbeute 51,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

1.7 g of [7-(tert-butoxycarbonyl)-7-azaspiro[3.5]non-2-yl]acetic acid was dissolved in 50 ml of dichloromethane. After adding 0.9 ml of triethylamine, the resulting mixture was ice-cooled. After adding 0.95 ml of ethyl chloroformate, the resulting mixture was stirred at room temperature for 30 minutes. Then 1.9 g of 3-amino-8-methyl-8-azabicyclo[3.2.1]octane dihydrochloride and 2.5 ml of triethylamine were added thereto and the resulting mixture was stirred at room temperature for 6 hours. After adding water, the reaction mixture was extracted with ethyl acetate. The organic layer was washed with 1 N sodium hydroxide and dried over anhydrous magnesium sulfate. After distilling off the solvent under reduced pressure, the obtained crystals were washed with ether to thereby give 1.25 g of the title compound as white crystals.

Aufarbeitung

  1. temperaturecooled
  2. stirringthe resulting mixture was stirred at room temperature for 6 hours
  3. extractionthe reaction mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with 1 N sodium hydroxide
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationAfter distilling off the solvent under reduced pressure
  7. washthe obtained crystals were washed with ether

Quellen und Nachweise

ORD-Eintrag
ord-8dfb3b473795422fb268f356f353d9b7
Quelldatensatz
uspto-grants-2003_02
Patentnummer
US06518423B1

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