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Hydrochloric Acid → 2-benzyl-6-hydroxymethyl-1-oxo-4-phenyl-1,2-dihydroisoquinoline-3-carboxylic Acid Methyl Ester

HRID 750174
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 750174
[CH3:1][O:2][C:3]([C:5]1[N:6]([CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:7](=[O:24])[C:8]2[C:13]([C:14]=1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[CH:12][C:11]([C:21](O)=[O:22])=[CH:10][CH:9]=2)=[O:4].O.Cl>C1COCC1>[CH3:1][O:2][C:3]([C:5]1[N:6]([CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:7](=[O:24])[C:8]2[C:13]([C:14]=1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[CH:12][C:11]([CH2:21][OH:22])=[CH:10][CH:9]=2)=[O:4]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 444517952-Benzyl-3-(methoxycarbonyl)-1-oxo-4-phenyl-1,2-dihydroisoquinoline-6-carboxylic acid

Produkt 1

HCID 691568552-benzyl-6-hydroxymethyl-1-oxo-4-phenyl-1,2-dihydroisoquinoline-3-carboxylic Acid Methyl EsterAusbeute 96,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028
Tetrahydrofuran
Lösungsmittel
3×

Versuchsvorschrift

To a solution of 2-benzyl-1-oxo-4-phenyl-1,2-dihydroisoquinoline-3,6-dicarboxylic acid 3-methyl ester (300 mg) in THF (3 ml) was added dropwise a solution (1M, 1.5 ml) of borane complex in THF under ice-cooling, and the mixture was allowed to warm to room temperature and stirred for 4 hrs. To the reaction mixture was further added dropwise a solution (1M, 3 ml) of borane complex in THF at room temperature, and the mixture was stirred for 1 hr. To the reaction mixture were added water and 10% hydrochloric acid under ice-cooling, and the mixture was extracted with ethyl acetate. The organic layer was washed with water, saturated aqueous sodium hydrogen carbonate, water and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The obtained residue was crystallized from ethyl acetate-hexane to give the title compound (280 mg).

Aufarbeitung

  1. temperaturecooling
  2. stirringthe mixture was stirred for 1 hr
  3. temperaturecooling
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe organic layer was washed with water, saturated aqueous sodium hydrogen carbonate, water and saturated brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe obtained residue was crystallized from ethyl acetate-hexane

Quellen und Nachweise

ORD-Eintrag
ord-32bfcfe8c0274daa836b7f9c24aa9453
Quelldatensatz
uspto-grants-2008_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07402595B2

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