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Benzyl Alcohol → 2-(Benzyloxycarbonylaminomethyl)indan

HRID 1289437
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1289437
[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH:2]1[CH2:10]C(O)=O.C([N:16]([CH2:19]C)CC)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:28])C=CC=CC=1.[CH2:38]([OH:45])[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1>C1(C)C=CC=CC=1>[CH2:38]([O:45][C:19]([NH:16][CH2:10][CH:2]1[CH2:1][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3]1)=[O:28])[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 244Benzyl AlcoholHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 51749552-(2,3-dihydro-1H-inden-2-yl)acetic Acid

Produkt 1

HCID 189214832-(Benzyloxycarbonylaminomethyl)indanAusbeute 86,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140
Toluene
Lösungsmittel

Versuchsvorschrift

Dissolved in 150 ml of toluene were 17.6 g (0.10 mol) of 2-(indan-2-yl)acetic acid, and 15.3 ml (0.11 mol) of triethyl-amine and 33.0 g (0.12 mol) of diphenylphosphoryl azide were added to the solution. After the mixture was stirred at room temperature for 30 minutes, 16.6 g (0.15 mol) of benzyl alcohol were added, and the resultant mixture was refluxed for 18 hours. After cooling the mixture, the solvent was distilled off under reduced pressure, and the residue was dissolved in 500 ml of ethyl acetate, washed with 1N sodium hydroxide and then concentrated. The resultant residue was purified by column chromatography on silica gel (ethyl acetate:hexane=1:3), and the resultant crystal was recrystallized from a mixed solvent of ethyl acetate and hexane to obtain 24.3 g of 2-(benzyloxycarbonylamino-methyl)indane as a colorless needle crystal. Yield: 86%.

Aufarbeitung

  1. additionwere added to the solution
  2. temperatureAfter cooling the mixture
  3. distillationthe solvent was distilled off under reduced pressure
  4. dissolutionthe residue was dissolved in 500 ml of ethyl acetate
  5. washwashed with 1N sodium hydroxide
  6. concentrationconcentrated
  7. customThe resultant residue was purified by column chromatography on silica gel (ethyl acetate:hexane=1:3)
  8. customthe resultant crystal was recrystallized from a mixed solvent of ethyl acetate and hexane

Quellen und Nachweise

ORD-Eintrag
ord-1de21c5e1be641ceb804a768ed55cbd6
Quelldatensatz
uspto-grants-1998_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05750524

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