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tert-Butyl 4-oxopiperidine-1-carboxylate → HCID 59865005, Verbindung

HRID 1669732
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Reaktionsgleichung

Reaktionsgleichung von HRID 1669732
I[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:9][CH2:10][CH2:11][N:12]2[CH2:17][CH2:16][CH2:15][C:14]([CH3:19])([CH3:18])[CH2:13]2)=[CH:4][CH:3]=1.[Li]CCCC.[C:25]([N:32]1[CH2:37][CH2:36][C:35](=[O:38])[CH2:34][CH2:33]1)([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26]>C1COCC1>[CH3:18][C:14]1([CH3:19])[CH2:15][CH2:16][CH2:17][N:12]([CH2:11][CH2:10][CH2:9][O:8][C:5]2[CH:6]=[CH:7][C:2]([C:35]3([OH:38])[CH2:34][CH2:33][N:32]([C:25]([O:27][C:28]([CH3:30])([CH3:29])[CH3:31])=[O:26])[CH2:37][CH2:36]3)=[CH:3][CH:4]=2)[CH2:13]1
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Komponenten

5

Edukt 3

HCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 59865001HCID 59865001, Verbindung2×HCID 178418339Butyllithium

Produkt 1

HCID 59865005HCID 59865005, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

A solution of 1-{3-[(4-iodophenyl)oxy]propyl}-3,3-dimethylpiperidine (for example as prepared for Intermediate 2) (3 g, 8.02 mmol) in anhydrous THF (30 ml) was cooled to −78° C. under nitrogen and treated with nBuLi (1.6M solution in hexanes, 6.02 ml, 9.63 mmol), after 0.5 h, a solution of N-Boc-4-oxopiperidine (commercially available, for example from Aldrich) (1.99 g, 10 mmol) in THF (10 ml) was added dropwise. The mixture was allowed to warm up to room temperature and was stirred overnight. The mixture was quenched with ammonium chloride solution and extracted with EtOAc, dried over magnesium sulphate, filtered and concentrated. The resulting residue was purified by FlashMaster II chromatography using a 100 g cartridge, eluting with 100% cyclohexane for 5 minutes, 100% cyclohexane to 100% EtOAc over 15 minutes, 100% EtOAc to 100% DCM in 5 minutes and 100% DCM to 30% MeOH (containing 1% of triethylamine) in DCM over 40 minutes then held constant for 5 min, monitoring at 254 nm to afford the title compound (1.25 g). LCMS RT=2.48 min, ES+ve m/z 447 (M+H)+.

Aufarbeitung

  1. customwas cooled to −78° C. under nitrogen
  2. customThe mixture was quenched with ammonium chloride solution
  3. extractionextracted with EtOAc
  4. dry with materialdried over magnesium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe resulting residue was purified by FlashMaster II chromatography
  8. washeluting with 100% cyclohexane for 5 minutes
  9. wait100% cyclohexane to 100% EtOAc over 15 minutes
  10. wait100% EtOAc to 100% DCM in 5 minutes
  11. wait100% DCM to 30% MeOH (containing 1% of triethylamine) in DCM over 40 minutes then held constant for 5 min

Quellen und Nachweise

ORD-Eintrag
ord-0df5c8eacb6b4879b419c6476397f312
Quelldatensatz
uspto-grants-2011_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07989629B2

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