StartseiteMCPWorkbenchSkills
StartseiteWorkbenchBenachrichtigungenMein Bereich
llms.txt · MCP-AnleitungDatenschutz · Nutzungsbedingungen · Supportv1.8.0
  1. Startseite
  2. /Reaktion

p-Toluenesulfonic acid → HCID 18367319, Verbindung

HRID 1741412
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1741412
[NH2:1][CH:2]1[C:10]2[C:5](=[C:6]([O:11][CH3:12])[CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3]1.[OH:13][CH2:14][CH2:15][CH2:16][C:17]([C:19]1[O:20][C:21]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)=[C:22]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[N:23]=1)=O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[OH:13][CH2:14][CH2:15][CH2:16][CH:17]([NH:1][CH:2]1[C:10]2[C:5](=[C:6]([O:11][CH3:12])[CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3]1)[C:19]1[O:20][C:21]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)=[C:22]([C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[N:23]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 6101p-Toluenesulfonic acidHCID 30167414-Methoxy-2,3-dihydro-1H-inden-1-amineHCID 18367218HCID 18367218, Verbindung

Produkt 1

HCID 18367319HCID 18367319, VerbindungAusbeute 32,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

A solution of 1-amino-2,3-dihydro-4-methoxy-1H-indene (0.30 g), 4-hydroxy-1-(4,5-diphenyloxazol-2-yl)butan-1-one (0.56 g) and p-toluenesulfonic acid (catalytic amount) in toluene (50 ml) was refluxed for 2 days with Dean-stark equipment. The solvent was evaporated in vacuo and the residue was dissolved in methanol (10 ml). To the methanol solution was added NaBH4 (0.20 g) at 0° C. After being stirred for 1 hour at the same temperature, the solvent was evaporated in vacuo and the residue was partitioned between ethyl acetate and sat. NaHCO3. The organic layer was washed with brine. The dried solvent was evaporated in vacuo. The residue was purified by chromatography on silica gel to give 1-[[4-hydroxy-1-(4,5-diphenyloxazol-2-yl)butyl]amino]-2,3-dihydro-4-methoxy-1H-indene (0.27 g). MS (m/z): 455 (M+ +1) NMR (CDCl3, δ): 1.60-3.20 (10H, m), 3.76 (2.5H, s), 3.84 (3.5H, s), 4.02-4.52 (2H, m), 7.59-7.69 (4H, m), 6.69-7.39 (9H, m)

Aufarbeitung

  1. customThe solvent was evaporated in vacuo
  2. dissolutionthe residue was dissolved in methanol (10 ml)
  3. additionTo the methanol solution was added NaBH4 (0.20 g) at 0° C
  4. customthe solvent was evaporated in vacuo
  5. customthe residue was partitioned between ethyl acetate and sat. NaHCO3
  6. washThe organic layer was washed with brine
  7. customThe dried solvent was evaporated in vacuo
  8. customThe residue was purified by chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-a03feda6e4fd4a759932c5ed4649774d
Quelldatensatz
uspto-grants-1999_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05972965

Notizen zur Reaktion

Wird geladen…

Auf dieser SeiteKomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion