1-Benzyl 4-methyl 4-allylpiperidine-1,4-dicarboxylate → 1-Benzyl 4-methyl 4-(2-oxoethyl)piperidine-1,4-dicarboxylate

HRID 1864915

Reaktionsgleichung

Reaktionsgleichung von HRID 1864915
[CH2:1]([C:4]1([C:20]([O:22][CH3:23])=[O:21])[CH2:9][CH2:8][N:7]([C:10]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[O:11])[CH2:6][CH2:5]1)[CH:2]=C.C1C=C[NH+]=CC=1.[O-:30][Cr](Cl)(=O)=O>C1COCC1.C(Cl)Cl.CCOCC>[O:30]=[CH:2][CH2:1][C:4]1([C:20]([O:22][CH3:23])=[O:21])[CH2:9][CH2:8][N:7]([C:10]([O:12][CH2:13][C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)=[O:11])[CH2:6][CH2:5]1

Komponenten

6

Edukt 2

HCID 588931861-Benzyl 4-methyl 4-allylpiperidine-1,4-dicarboxylateHCID 178418287HCID 178418287, Verbindung

Produkt 1

HCID 588931821-Benzyl 4-methyl 4-(2-oxoethyl)piperidine-1,4-dicarboxylate

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 3283Diethyl EtherLösungsmittelHCID 6344DichloromethaneLösungsmittelHCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a solution of 1-benzyl 4-methyl 4-allylpiperidine-1,4-dicarboxylate from Step B (4.45 g, 14.0 mmol) in THF (70 mL) at 0° C. was added borane-methyl sulfide complex (28.0 mL of a 2M solution in THF, 56.1 mmol). The reaction mixture was slowly warmed to ambient temperature and stirred for 16 h, then quenched with water and concentrated in vacuo. The residue was dissolved in CH2Cl2 (140 mL) and added drop wise to a solution of PCC (6.65 g. 30.8 mmol) and 4 Å molecular sieves (6.65 g) in CH2Cl2 (50 mL) at 0° C. The reaction mixture was warmed to ambient temperature and stirred for 16 h, then diluted with ether (200 mL) and filtered through a pad of celite. Additional ether was used to wash the celite. The combined organics were concentrated in vacuo to give a residue that was purified by silica gel chromatography, eluting with a gradient of CH2Cl2:MeOH-100:0 to 95:5, to give the title compound. MS: m/z=356 (M+Na).

Aufarbeitung

  1. customquenched with water
  2. concentrationconcentrated in vacuo
  3. dissolutionThe residue was dissolved in CH2Cl2 (140 mL)
  4. temperatureThe reaction mixture was warmed to ambient temperature
  5. stirringstirred for 16 h
  6. filtrationfiltered through a pad of celite
  7. washto wash the celite
  8. concentrationThe combined organics were concentrated in vacuo
  9. customto give a residue that
  10. customwas purified by silica gel chromatography
  11. washeluting with a gradient of CH2Cl2

Quellen und Nachweise

ORD-Eintrag
ord-9495b06a2b7f47d689f4fb3ebd02d74b
Quelldatensatz
uspto-grants-2009_12
Patentnummer
US07625901B2

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