Potassium Carbonate → cis-2-[(2-hydroxycyclohexyl)methyl]-1H-isoindole-1,3(2H)-dione

HRID 1269945Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1269945
C(=O)([O-])[O-].[K+].[K+].C(OC([C:12]1[CH:22]=[CH:21][CH:20]=[C:14]2[C:15]([NH:17][C:18](=[O:19])[C:13]=12)=[O:16])=O)C.Cl.N[CH2:25][CH:26]1[CH2:31][CH2:30][CH2:29][CH2:28][CH:27]1[OH:32]>O>[OH:32][C@H:27]1[CH2:28][CH2:29][CH2:30][CH2:31][C@H:26]1[CH2:25][N:17]1[C:18](=[O:19])[C:13]2[C:14](=[CH:20][CH:21]=[CH:22][CH:12]=2)[C:15]1=[O:16]

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 22254400EthoxycarbonylphthalimideHCID 229334442-(Aminomethyl)cyclohexanol hydrochloride

Produkt 1

HCID 69430762cis-2-[(2-hydroxycyclohexyl)methyl]-1H-isoindole-1,3(2H)-dioneAusbeute 75 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

Under a nitrogen atmosphere, potassium carbonate (375 mg, 2.72 mmol) and ethoxycarbonylphthalimide (364 mg, 1.66 mmol) were added to an aqueous solution (4 ml) of 2-aminomethylcyclohexanol hydrochloride (250 mg, 1.51 mmol) at room temperature. After 3 hours, the reaction solution was poured into water and extracted with ethyl acetate, and the organic layer was dried over anhydrous magnesium sulfate. The organic layer dried was concentrated under reduced pressure and the resulting residue was purified by a silica gel column chromatography (eluent: hexane/ethyl acetate) to obtain cis-2-[(2-hydroxycyclohexyl)methyl]-1H-isoindole-1,3(2H)-dione (291.6 mg, 75%).

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  3. customThe organic layer dried
  4. concentrationwas concentrated under reduced pressure
  5. customthe resulting residue was purified by a silica gel column chromatography (eluent: hexane/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-8ca25552dbb24459b79770905aa96bc0
Quelldatensatz
uspto-grants-2007_04
Patentnummer
US07199147B2

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