3-Phenylpyridine → 1-(2,3-Dihydrobenzo[1,4]dioxin-2-ylmethyl)-5-phenyl-1,2,3,6-tetrahydropyridine

HRID 2365937Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2365937
Br[CH2:2][CH:3]1[O:8][C:7]2[CH:9]=[CH:10][CH:11]=[CH:12][C:6]=2[O:5][CH2:4]1.[C:13]1([C:19]2[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[BH4-].[Na+]>C1(C)C(C)=CC=CC=1.CO>[O:8]1[C:7]2[CH:9]=[CH:10][CH:11]=[CH:12][C:6]=2[O:5][CH2:4][CH:3]1[CH2:2][N:21]1[CH2:20][C:19]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:24][CH2:23][CH2:22]1

Komponenten

6

Edukt 3

HCID 138863-PhenylpyridineHCID 983332-Bromomethyl-1,4-benzodioxaneHCID 4311764Sodium borohydride

Produkt 1

HCID 251745131-(2,3-Dihydrobenzo[1,4]dioxin-2-ylmethyl)-5-phenyl-1,2,3,6-tetrahydropyridine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 7237O-XyleneLösungsmittel

Versuchsvorschrift

A mixture of 2-bromomethyl-2,3-dihydrobenzo[1,4]dioxine (500 mg, 2.18 mmol) and 3-phenyl-pyridine (339 mg, 2.18 mmol) in xylene (2 ml) was refluxed for 4 h. After cooling, the solvent was decanted to give the crude oily pyridinium salt, which was dissolved in MeOH (5 ml). NaBH4 (330 mg, 4 eq) was added in small portions to the cooled mixture. After stirring for 2 h at RT, MeOH was evaporated, water was added and the mixture extracted with EtOAc. Drying (Na2SO4) and evaporation gave the crude product, which was purified by flash chromatography (heptane/EtOAc).

Aufarbeitung

  1. temperaturewas refluxed for 4 h
  2. temperatureAfter cooling
  3. customthe solvent was decanted
  4. customto give the crude oily pyridinium salt, which
  5. customMeOH was evaporated
  6. additionwater was added
  7. extractionthe mixture extracted with EtOAc
  8. customDrying
  9. custom(Na2SO4) and evaporation

Quellen und Nachweise

ORD-Eintrag
ord-0dc3697f31a4433bad47d80f5b9c2f0d
Quelldatensatz
uspto-grants-2014_04
Patentnummer
US08697723B2

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