Tetrahydrofuran → 6,7-dihydro-5H-cyclopenta[c]pyridin-3-ylmethanol

HRID 1943162Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1943162
[CH:1]1[C:6]2[CH2:7][CH2:8][CH2:9][C:5]=2[CH:4]=[C:3]([C:10](OCC)=[O:11])[N:2]=1.C1COCC1.[H-].[H-].[H-].[H-].[Li+].[Al+3].[OH-].[Na+]>O>[CH:1]1[C:6]2[CH2:7][CH2:8][CH2:9][C:5]=2[CH:4]=[C:3]([CH2:10][OH:11])[N:2]=1

Komponenten

6

Edukt 4

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 14735905Ethyl 6,7-dihydro-5H-cyclopenta[c]pyridine-3-carboxylateHCID 21226445Aluminium lithium hydride

Produkt 1

HCID 685981886,7-dihydro-5H-cyclopenta[c]pyridin-3-ylmethanolAusbeute 57 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel2×

Versuchsvorschrift

A solution of ethyl 6,7-dihydro-5H-cyclopenta[c]pyridine-3-carboxylate (427 mg, 2.233 mmol) in (THF) (20 ml) at −78° C. under argon was treated with LiAlH4 (1M in THF) (2.233 ml, 2.233 mmol) and allowed warm to rt. After 10 min at rt, water (1 ml), 2M aq NaOH (1 ml) and water (1 ml) were sequentially added and the mixture stirred at rt for 0.5 h. The mixture was then filtered through a short pad of Kieselguhr, eluting with THF (50 ml), organic extracts were then evaporated, chromatographed (0-20% methanol/DCM) to give product as an orange oil (189 mg, 57%).

Aufarbeitung

  1. filtrationThe mixture was then filtered through a short pad of Kieselguhr
  2. washeluting with THF (50 ml), organic extracts
  3. customwere then evaporated
  4. customchromatographed (0-20% methanol/DCM)

Quellen und Nachweise

ORD-Eintrag
ord-f29bbf7464454e999db688c28c5c919f
Quelldatensatz
uspto-grants-2013_03
Patentnummer
US08389524B2

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