Ethyl Acetate → 4-Chloro-6,7-dihydro-5H-cyclopenta[b]pyridin-7-ol

HRID 44571

Reaktionsgleichung

Reaktionsgleichung von HRID 44571
C(N([CH2:8][CH3:9])C(C)C)(C)C.[ClH:10].Br[C:12]1[CH:17]=[CH:16][N:15]=[CH:14][CH:13]=1.[C:18](=[O:21])([O-])[O-].[K+].[K+].CCOC(C)=O>C(#N)C>[Cl:10][C:12]1[CH:17]=[CH:16][N:15]=[C:14]2[CH:18]([OH:21])[CH2:8][CH2:9][C:13]=12

Komponenten

6

Edukt 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 81531DiisopropylethylamineHCID 881004-Bromopyridinium chloride

Produkt 1

HCID 569657354-Chloro-6,7-dihydro-5H-cyclopenta[b]pyridin-7-ol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

A solution of intermediate 11 (0.0031 mol), N,N-diisopropylethylamine (0.0028 mol), 4-bromopyridine hydrochloride (0.0034 mol) in acetonitrile (20 ml) was heated at 65° C. for 6 hours. Potassium carbonate 10% and EtOAc were added. The reaction mixture was extracted, the organic layer was separated, dried over MgSO4, filtered and concentrated. The residue (1.3 g) was purified by column chromatography over silica gel (eluent 95/5/0.5 DCM/MeOH/NH4OH). Two fractions were collected and the solvent was evaporated to give 60 mg of compound 3 and 80 mg of F2. The residue F2 (80 mg) was purified by supercritical fluid chromatography (AMINO column 150×21.2 mmm) eluent: MeOH/CO2 30/70). The pure fractions were collected and the solvent was evaporated, yielding 43 mg of compound 2.

Aufarbeitung

  1. extractionThe reaction mixture was extracted
  2. customthe organic layer was separated
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue (1.3 g) was purified by column chromatography over silica gel (eluent 95/5/0.5 DCM/MeOH/NH4OH)
  7. customTwo fractions were collected
  8. customthe solvent was evaporated

Quellen und Nachweise

ORD-Eintrag
ord-15259eef555f43be9da38e1f1861a416
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08541442B2

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