N-Hydroxyphthalimide → 2-((1H-imidazol-2-yl)methoxy)isoindoline-1,3-dione

HRID 1821828

Reaktionsgleichung

Reaktionsgleichung von HRID 1821828
Cl.[NH:2]1[CH:6]=[CH:5][N:4]=[C:3]1[CH2:7][OH:8].O[N:10]1[C:14](=[O:15])[C:13]2=[CH:16][CH:17]=[CH:18][CH:19]=[C:12]2[C:11]1=[O:20].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C1COCC1>[NH:2]1[CH:6]=[CH:5][N:4]=[C:3]1[CH2:7][O:8][N:10]1[C:14](=[O:15])[C:13]2[C:12](=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:11]1=[O:20]

Komponenten

6

Edukt 4

HCID 10665N-HydroxyphthalimideHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 27762781H-imidazol-2-ylmethanol Hydrochloride

Produkt 1

HCID 689843332-((1H-imidazol-2-yl)methoxy)isoindoline-1,3-dioneAusbeute 6,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To an ice-cold solution of (1H-imidazol-2-yl)methanol hydrochloride (2.0 g, 15 mmol), N-hydroxyphthalimide (2.4 g, 15 mmol) and triphenylphosphine (4.0 g, 15 mmol) in THF (65 mL) was added a solution of diethyl azodicarboxylate (2.6 mL, 16 mmol) in THF (10 mL) dropwise. The stirred reaction mixture was allowed to warm to ambient temperature. After 1 day, most of the THF was removed under reduced pressure. The residue was partitioned between CH2Cl2 (75 ml) and H2O (30 mL). The organic layer was separated and washed with saturated NaHCO3 (75 mL) and saturated NaCl (20 ml), dried (Na2SO4) and concentrated under reduced pressure. Purification by column chromatography (silica gel, CH2Cl2 to 95:5 CH2Cl2/MeOH) gave 2-(1H-imidazol-2-ylmethoxy)-1,3-dihydro-2H-isoindole-1,3-dione (240 mg, 6.5%) which was used directly in the next reaction.

Aufarbeitung

  1. customThe stirred reaction mixture
  2. custommost of the THF was removed under reduced pressure
  3. customThe residue was partitioned between CH2Cl2 (75 ml) and H2O (30 mL)
  4. customThe organic layer was separated
  5. washwashed with saturated NaHCO3 (75 mL) and saturated NaCl (20 ml)
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated under reduced pressure
  8. customPurification by column chromatography (silica gel, CH2Cl2 to 95:5 CH2Cl2/MeOH)

Quellen und Nachweise

ORD-Eintrag
ord-1f4a7513e2314a8ca524810f33ae7df1
Quelldatensatz
uspto-grants-2009_10
Patentnummer
US07608627B2

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