Water → 1-(2-Methoxy-4-nitro-benzyl)-piperidine

HRID 1993521Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1993521
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([N+:9]([O-:11])=[O:10])[CH:6]=[CH:5][C:4]=1[C:12]([N:14]1[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1)=O.CC(C[AlH]CC(C)C)C.O>C1COCC1>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([N+:9]([O-:11])=[O:10])[CH:6]=[CH:5][C:4]=1[CH2:12][N:14]1[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1

Komponenten

5

Edukt 3

HCID 962WaterHCID 14487Diisobutylaluminum hydride2×HCID 68540547(2-Methoxy-4-nitro-phenyl)-piperidin-1-yl-methanone

Produkt 1

HCID 685371561-(2-Methoxy-4-nitro-benzyl)-piperidine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

(2-Methoxy-4-nitro-phenyl)-piperidin-1-yl-methanone (Stage 87.3; 200 mg, 0.76 mmol) is dissolved in THF (8 ml) at −20° C. DIBAH (1 M in THF: 2.3 ml) then is added. After 90 min at −20° C., another portion of DIBAH (0.8 ml) is added and stirring continued for 2 h. Then the reaction mixture is hydrolysed by water (30 ml) and a saturated solution of sodium potassium tartrate (25 ml) and extracted 3 times with AcOEt. The organic phases are washed with brine, dried (Na2SO4) and concentrated. The crude product is dissolved in AcOEt, SiO2 is then added and the solvent evaporate off in vacuo. The resulting powder is put on top of a chromatography column (SiO2; AcOEt) and the title compound eluated with AcOEt: 1H-NMR (DMSO-d6): 7.83 (dd, 1H), 7.73 (d, 1H), 7.60 (d, 1H), 3.91 (s, H3CO), 3.49 (s, 2H), 2.36 (m, 4H), 1.52 (m, 4H), 1.39 (m, 2H).

Aufarbeitung

  1. waitcontinued for 2 h
  2. extractiona saturated solution of sodium potassium tartrate (25 ml) and extracted 3 times with AcOEt
  3. washThe organic phases are washed with brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. dissolutionThe crude product is dissolved in AcOEt
  7. additionSiO2 is then added
  8. customthe solvent evaporate off in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-7c2d446ade8b4b73aaf5a590629f211b
Quelldatensatz
uspto-grants-2010_01
Patentnummer
US07652022B2

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