Phthalimide → N-[[1-[2-(Methoxycarbonyl)phenyl]piperidin-3-yl]methyl]phthalimide

HRID 602164

Reaktionsgleichung

Reaktionsgleichung von HRID 602164
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:20]1(=[O:30])[NH:24][C:23](=[O:25])[C:22]2=[CH:26][CH:27]=[CH:28][CH:29]=[C:21]12.O[CH2:32][CH:33]1[CH2:38][CH2:37][CH2:36][N:35]([C:39]2[CH:48]=[CH:47][CH:46]=[CH:45][C:40]=2[C:41]([O:43][CH3:44])=[O:42])[CH2:34]1.N(C(OCC)=O)=NC(OCC)=O.C1(C)C=CC=CC=1>O1CCCC1.O>[CH3:44][O:43][C:41]([C:40]1[CH:45]=[CH:46][CH:47]=[CH:48][C:39]=1[N:35]1[CH2:36][CH2:37][CH2:38][CH:33]([CH2:32][N:24]2[C:20](=[O:30])[C:21]3=[CH:29][CH:28]=[CH:27][CH:26]=[C:22]3[C:23]2=[O:25])[CH2:34]1)=[O:42]

Komponenten

7

Edukt 4

HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 58992598Methyl 2-[3-(hydroxymethyl)piperidin-1-yl]benzoateHCID 66777355Diethylazodicarboxylate toluene

Produkt 1

HCID 58992691N-[[1-[2-(Methoxycarbonyl)phenyl]piperidin-3-yl]methyl]phthalimideAusbeute 95 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Triphenylphosphine (1.68 g, 6.20 mmol) and phthalimide (799 mg, 5.43 mmol) were added to methyl 2-[3-(hydroxymethyl)piperidin-1-yl]benzoate (1.29 g, 5.17 mmol) in tetrahydrofuran (10 mL). The reaction mixture was stirred at room temperature for 10 min and a 40% diethyl azodicarboxylate/toluene solution (3.52 mL, 7.76 mmol) was added. The mixture was then stirred at room temperature for 8 hours. Subsequently, water was added and the mixture was extracted with ethylacetate. The extract was washed with brine, followed by drying over magnesium sulfate and evaporation of the solvent. Purification of the resulting residue by silica gel column chromatography (hexane:ethyl acetate=20:1->5:1) gave 1.85 g (95%) of the desired compound as a pale yellow oil.

Aufarbeitung

  1. stirringThe mixture was then stirred at room temperature for 8 hours
  2. extractionthe mixture was extracted with ethylacetate
  3. washThe extract was washed with brine
  4. dry with materialby drying over magnesium sulfate and evaporation of the solvent
  5. customPurification of the resulting residue by silica gel column chromatography (hexane:ethyl acetate=20:1->5:1)

Quellen und Nachweise

ORD-Eintrag
ord-0cc93c605ff844d78e7a84d99a0d7f4f
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07902367B2

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