Borane;tetrahydrofuran → Methyl 3-(piperidin-1-yl)benzoate

HRID 2336

Reaktionsgleichung

Reaktionsgleichung von HRID 2336
O=[C:2]1[CH2:7][CH2:6][CH2:5][CH2:4][N:3]1[C:8]1[CH:9]=[C:10]([CH:15]=[CH:16][CH:17]=1)[C:11]([O:13][CH3:14])=[O:12].B.O1CCCC1>C1COCC1>[N:3]1([C:8]2[CH:9]=[C:10]([CH:15]=[CH:16][CH:17]=2)[C:11]([O:13][CH3:14])=[O:12])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:2]1

Komponenten

4

Edukt 2

HCID 2723981Borane;tetrahydrofuranHCID 10681135Methyl 3-(2-oxopiperidin-1-yl)benzoate

Produkt 1

HCID 7148413Methyl 3-(piperidin-1-yl)benzoateAusbeute 90 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

The compound of Example 37 (640 mg, 2.75 mmol) was dissolved in dry THF (30 ml) and borane-tetrahydrofuran complex (5 ml, 1M solution in THF) was added. The mixture was stirred under nitrogen under reflux for 1 h, then cooled and evaporated. The residue was taken up in MeOH/acetic acid (6/1, v/v, 70 ml) and heated under reflux for 3 h, then evaporated and chromatographed (eluant 10% EtOAc in hexanes) to provide a colourless oil (540 mg, 90%).

Aufarbeitung

  1. temperatureunder reflux for 1 h
  2. temperaturecooled
  3. customevaporated
  4. temperatureheated
  5. temperatureunder reflux for 3 h
  6. customevaporated
  7. customchromatographed (eluant 10% EtOAc in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-b2a2fb45af4f44099c49615f8d09865c
Quelldatensatz
uspto-grants-1998_03
Patentnummer
US05728829

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