Tetrahydrofuran → N-[(3R)-1-azabicyclo[2.2.2]oct-3-yl]-2,2-dithien-2-ylacetamide

HRID 2237614

Reaktionsgleichung

Reaktionsgleichung von HRID 2237614
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH:6]([C:10]1[S:11][CH:12]=[CH:13][CH:14]=1)[C:7]([OH:9])=O.[C:15]([N:22]1[CH:26]=[CH:25][N:24]=[CH:23]1)(N1C=CN=C1)=O.[N-]1C=CN=C1.[CH2:32]1[CH2:36]OC[CH2:33]1>CCOCC>[N:22]12[CH2:15][CH2:36][CH:32]([CH2:33][CH2:23]1)[C@@H:25]([NH:24][C:7](=[O:9])[CH:6]([C:2]1[S:1][CH:5]=[CH:4][CH:3]=1)[C:10]1[S:11][CH:12]=[CH:13][CH:14]=1)[CH2:26]2

Komponenten

6

Edukt 4

HCID 8028TetrahydrofuranHCID 20443Di(2-thienyl)acetic acidHCID 682631,1'-CarbonyldiimidazoleHCID 3386966Imidazolate

Produkt 1

HCID 9996901N-[(3R)-1-azabicyclo[2.2.2]oct-3-yl]-2,2-dithien-2-ylacetamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

2,2-dithien-2-ylacetic acid was produced by hydrolysis of 2,2-dithien-2-ylacetic acid methyl ester, previously prepared as described in F. Leonard and I. Ehranthal, J. Am. Chem. Soc, (1951), Vol 73, page 2216. 1.2 g (0.0054 mot) of 2,2-dithien-2-ylacetic acid were dissolved in 25 ml of THF. To this solution were added 0.96 g (0.00594 mol) of 1,1′-carbonyldiimidazole and the mixture was refluxed for an hour. The reaction was monitored by TLC following the formation of the imidazolide. When the reaction was completed 0.75 g (0.00594 mol) of (3R)-aminoquinuclidine were added. The reaction mixture was refluxed for 16 h, cooled, diluted with ether and washed with water. The organic layer was extracted with HCl-2N, the acid solution basified with K2CO3 and extracted with CHCl3. The organic phase was dried over Na2SO4 and the solvent was evaporated to obtain 0.60 g of an oil which was purified by column chromatography (silica gel, CHCl3:MeOH:NH4OH 90:10:1 as eluent). Appropriate fractions were combined and evaporated to give 0.31 g of the title product (17.3%).

Aufarbeitung

  1. custompreviously prepared
  2. temperaturethe mixture was refluxed for an hour
  3. additionwere added
  4. temperatureThe reaction mixture was refluxed for 16 h
  5. temperaturecooled
  6. washwashed with water
  7. extractionThe organic layer was extracted with HCl-2N
  8. extractionextracted with CHCl3
  9. dry with materialThe organic phase was dried over Na2SO4
  10. customthe solvent was evaporated

Quellen und Nachweise

ORD-Eintrag
ord-2691ab66d61445f2927f7459175def0e
Quelldatensatz
uspto-grants-2010_05
Patentnummer
US07718670B2

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