Water → 5-t-Butoxycarbonyl-2-methyl-4,5,6,7-tetrahydro-thieno[3,2-c]pyridine

HRID 2301120Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2301120
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]2[S:14][CH:15]=[CH:16][C:10]=2[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:17]CCCCC.C([Li])CCC.CI.O>O1CCCC1>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]2[S:14][C:15]([CH3:17])=[CH:16][C:10]=2[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Komponenten

6

Edukt 4

HCID 962WaterHCID 6328Methyl iodideHCID 18377286tert-butyl 4H,5H,6H,7H-thieno[3,2-c]pyridine-5-carboxylateHCID 178418244HCID 178418244, Verbindung

Produkt 1

HCID 183773565-t-Butoxycarbonyl-2-methyl-4,5,6,7-tetrahydro-thieno[3,2-c]pyridine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

5-t-Butoxycarbonyl-4,5,6,7-tetrahydro-thieno[3,2-c]pyridine (330 mg, 1.4 mmol) was dissolved in anhydrous tetrahydrofuran (18 ml), n-butyl lithium hexane solution (3.0 mmol) was added dropwise to the solution which was cooled in an ice bath, and then the mixture was stirred for 1 hour. This was further mixed with methyl iodide (430 mg, 3.0 mmol), and the stirring was continued while increasing the reaction temperature to room temperature spending 2 hours. The reaction solution was mixed with water and the reaction product was extracted therefrom with ethyl acetate. The organic layer was washed with saturated brine and dried with anhydrous magnesium sulfate, and then the solvent was removed by evaporation under a reduced pressure and the thus obtained material was separated and purified by a silica gel column chromatography to obtain 110 mg (0.42 mmol, 31% in yield) of the title compound.

Aufarbeitung

  1. temperaturewas cooled in an ice bath
  2. waitspending 2 hours
  3. extractionthe reaction product was extracted
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried with anhydrous magnesium sulfate
  6. customthe solvent was removed by evaporation under a reduced pressure
  7. customthe thus obtained material was separated
  8. custompurified by a silica gel column chromatography
  9. customto obtain

Quellen und Nachweise

ORD-Eintrag
ord-2bb7b56485104658bb86fc591a33f5a7
Quelldatensatz
uspto-grants-2002_12
Patentnummer
US06498251B1

Notizen zur Reaktion

Wird geladen…