3-Benzo[1,3]dioxol-5-ylmethyl-1-benzyl-piperidin-2-one → (+)-3-Benzo[1,3]dioxol-5-ylmethyl-1-benzyl-piperidine

HRID 2354563Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2354563
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH2:10][CH:11]3[CH2:16][CH2:15][CH2:14][N:13]([CH2:17][C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)[C:12]3=O)=[CH:9][C:4]=2[O:3][CH2:2]1>C1COCC1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH2:10][CH:11]3[CH2:16][CH2:15][CH2:14][N:13]([CH2:17][C:18]4[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=4)[CH2:12]3)=[CH:9][C:4]=2[O:3][CH2:2]1

Komponenten

4

Edukt 1

HCID 684532313-Benzo[1,3]dioxol-5-ylmethyl-1-benzyl-piperidin-2-one

Produkt 1

HCID 68451530(+)-3-Benzo[1,3]dioxol-5-ylmethyl-1-benzyl-piperidine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittel2×HCID 21226445Aluminium lithium hydrideLösungsmittel

Versuchsvorschrift

To a solution of (−)-3-benzo[1,3]dioxol-5-ylmethyl-1-benzyl-piperidin-2-one (1.73 g, 5.3 mmol) in THF (21 ml), LiAlH4 (6.5 ml of a 1 M solution in THF, 6.5 mmol) is added dropwise at rt. The mixture is refluxed for 2.5 h, cooled to rt, quenched with water and filtered over Celite®. The filtrate is evaporated, the residue dissolved in AcOEt, washed with water and brine, and the aq. layers are reextracted with AcOEt, the combined organic layers are dried over Na2SO4 and evaporated to give (+)-3-benzo[1,3]dioxol-5-ylmethyl-1-benzyl-piperidine ([α]Drt=28.2° (c=0.5, EtOH)).

Aufarbeitung

  1. temperatureThe mixture is refluxed for 2.5 h
  2. customquenched with water
  3. filtrationfiltered over Celite®
  4. customThe filtrate is evaporated
  5. dissolutionthe residue dissolved in AcOEt
  6. washwashed with water and brine
  7. dry with materialthe combined organic layers are dried over Na2SO4
  8. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-6f0cb2e9a35c4679ab5f51723e69fac4
Quelldatensatz
uspto-grants-2010_07
Patentnummer
US07754719B2

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