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Phthalic Anhydride → 1H-Isoindole-1,3(2H)-dione, 2-[(1R)-2-hydroxy-1-phenylethyl]-

HRID 709435
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 709435
[NH2:1][C@H:2]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[CH2:3][OH:4].[C:11]1(=O)[O:16][C:14](=[O:15])[C:13]2=[CH:17][CH:18]=[CH:19][CH:20]=[C:12]12>CC#N>[OH:4][CH2:3][C@H:2]([N:1]1[C:14](=[O:15])[C:13]2[C:12](=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:11]1=[O:16])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

4

Edukt 2

HCID 6811Phthalic AnhydrideHCID 2724025(R)-beta-aminophenethyl alcohol

Produkt 1

HCID 112309321H-Isoindole-1,3(2H)-dione, 2-[(1R)-2-hydroxy-1-phenylethyl]-Ausbeute 94 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
150 °C

Versuchsvorschrift

To a 2.0-5.0 mL microwave vial was added (R)-2-amino-2-phenylethan-1-ol (1.53 g, 0.0112 mol) and phthalic anhydride (1.65 g, 0.0112 mol). The reaction mixture was capped and heated to 150° C. for 2 minutes in a microwave reactor. The mixture was cooled and diluted with CH3CN (2 mL), recapped and heated in the microwave reactor a second time at 140° C. for 20 minutes. The volatiles were removed under reduced pressure and the resulting solid was suspended in EtOAc (50 mL). The organic layer was washed with 5% NaHCO3 (aq), H2O, and brine, dried with anhydrous MgSO4 and concentrated. The crude residue was purified by flash chromatography (silica gel, eluting with CH3OH in CH2Cl2 (0 to 5%) to yield 2.81 g (94%) of the title compound. LC/MS: m/z (ES+) 268 (M+H)+.

Aufarbeitung

  1. customThe reaction mixture was capped
  2. temperatureThe mixture was cooled
  3. temperatureheated in the microwave reactor a second time at 140° C. for 20 minutes
  4. customThe volatiles were removed under reduced pressure
  5. washThe organic layer was washed with 5% NaHCO3 (aq), H2O, and brine
  6. dry with materialdried with anhydrous MgSO4
  7. concentrationconcentrated
  8. customThe crude residue was purified by flash chromatography (silica gel
  9. washeluting with CH3OH in CH2Cl2 (0 to 5%)

Quellen und Nachweise

ORD-Eintrag
ord-f3f00e6b29734919a2382577ac393684
Quelldatensatz
uspto-grants-2015_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09181200B2

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