Phthalimide → tert-Butyl 2-((1,3-dioxoisoindolin-2-yl)methyl)morpholine-4-carboxylate

HRID 602130

Reaktionsgleichung

Reaktionsgleichung von HRID 602130
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.[C:31]([O:35][C:36]([N:38]1[CH2:43][CH2:42][O:41][CH:40]([CH2:44]O)[CH2:39]1)=[O:37])([CH3:34])([CH3:33])[CH3:32].N(C(OCC)=O)=NC(OCC)=O.C1(C)C=CC=CC=1>O1CCCC1.C(OCC)(=O)C>[C:31]([O:35][C:36]([N:38]1[CH2:43][CH2:42][O:41][CH:40]([CH2:44][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])[CH2:39]1)=[O:37])([CH3:34])([CH3:32])[CH3:33]

Komponenten

7

Edukt 4

HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 5201202tert-Butyl 2-(hydroxymethyl)morpholine-4-carboxylateHCID 66777355Diethylazodicarboxylate toluene

Produkt 1

HCID 58992660tert-Butyl 2-((1,3-dioxoisoindolin-2-yl)methyl)morpholine-4-carboxylateAusbeute 97 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Triphenylphosphine (506 mg, 1.87 mmol) and phthalimide (275 mg, 1.87 mmol) were added to 4-(tert-butoxycarbonyl)morpholin-2-yl methanol (340 mg, 1.56 mmol) in tetrahydrofuran (3 mL). The mixture was stirred at room temperature for 5 min, followed by addition of a 40% diethyl azodicarboxylate/toluene solution (1.06 mL, 2.34 mmol) and stirring at room temperature for 4 hours. Subsequently, ethyl acetate was added and the mixture washed sequentially with tap water and brine. The mixture was then dried over magnesium sulfate and the solvent was evaporated. Purification of the residue by silica gel column chromatography (hexane:ethyl acetate=10:1->3:1) gave 524 mg (97%) of the desired compound as a colorless powder.

Aufarbeitung

  1. stirringstirring at room temperature for 4 hours
  2. washthe mixture washed sequentially
  3. dry with materialThe mixture was then dried over magnesium sulfate
  4. customthe solvent was evaporated
  5. customPurification of the residue by silica gel column chromatography (hexane:ethyl acetate=10:1->3:1)

Quellen und Nachweise

ORD-Eintrag
ord-68037ced14ef487da4480e0c343604ce
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07902367B2

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