Benzyl Bromide → Dimethyl 1-benzylpiperidine-3,5-dicarboxylate

HRID 1093050

Reaktionsgleichung

Reaktionsgleichung von HRID 1093050
[NH:1]1[CH2:6][CH:5]([C:7]([O:9][CH3:10])=[O:8])[CH2:4][CH:3]([C:11]([O:13][CH3:14])=[O:12])[CH2:2]1.C([O-])([O-])=O.[K+].[K+].[CH2:21](Br)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>C(#N)C>[CH2:21]([N:1]1[CH2:2][CH:3]([C:11]([O:13][CH3:14])=[O:12])[CH2:4][CH:5]([C:7]([O:9][CH3:10])=[O:8])[CH2:6]1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Komponenten

5

Edukt 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 49761012Dimethyl piperidine-3,5-dicarboxylate

Produkt 1

HCID 57905194Dimethyl 1-benzylpiperidine-3,5-dicarboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
23 °C

Versuchsvorschrift

To dimethyl piperidine-3,5-dicarboxylate (7.5 g, 37.3 mmol) in acetonitrile (100 mL) was added K2CO3 (20.6 g, 149.1) and benzylbromide (4.43 mL, 37.3 mmol). The reaction mixture was stirred at 23° C. for 4 hours. The K2CO3 was removed by filtration and the solvent evaporated in vacuo. A solution of NaHCO3 (1M, 150 mL) was added and the organic material extracted with ethyl acetate (3×50 mL), then dried (MgSO4) and concentrated in vacuo. The crude material was purified on a Silica gel column (Biotage flash chromatography system), eluting with a gradient of ethyl acetate/hexane (10:90) to (35:65) to afford the title compound as the cis diastereomer 1.6 g which eluted after the corresponding trans diastereomer. (based on the NMR reported in Synthetic Communications 1997, 27 (1), 69-71.). 1H NMR (400 MHz, CDCl3) δ ppm 7.26-7.36 (5 H, m), 3.68 (6 H, s), 3.59 (2 H, s), 3.15 (2 H, m), 2.66 (2 H, t, J=12.0 Hz), 2.36 (1 H, d, J=13.1 Hz), 2.05 (2 H, t, J=11.4 Hz), 1.56 (1 H, q, J=12.9 Hz). LCMS (+ESI, M+H+) m/z: 292.

Aufarbeitung

  1. customThe K2CO3 was removed by filtration
  2. customthe solvent evaporated in vacuo
  3. additionA solution of NaHCO3 (1M, 150 mL) was added
  4. extractionthe organic material extracted with ethyl acetate (3×50 mL)
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. customThe crude material was purified on a Silica gel column (Biotage flash chromatography system)
  8. washeluting with a gradient of ethyl acetate/hexane (10:90) to (35:65)

Quellen und Nachweise

ORD-Eintrag
ord-a8d743b53e9a43c3bfef7c47d4d1cd2a
Quelldatensatz
uspto-grants-2012_03
Patentnummer
US08129398B2

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