Hydrochloric Acid → HCID 11068249, Verbindung

HRID 324622Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 324622
[CH2:1]([C:4]1[C:5]([OH:21])=[C:6]([Br:20])[CH:7]=[C:8]2[C:12]=1[C@H:11]([CH2:13][CH2:14][NH:15][C:16](=[O:19])[CH2:17][CH3:18])[CH2:10][CH2:9]2)[CH:2]=C.[O:22]=[O+][O-].[BH4-].[Na+].Cl>CO>[Br:20][C:6]1[CH:7]=[C:8]2[C:12](=[C:4]([CH2:1][CH2:2][OH:22])[C:5]=1[OH:21])[C@H:11]([CH2:13][CH2:14][NH:15][C:16](=[O:19])[CH2:17][CH3:18])[CH2:10][CH2:9]2

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 24823OzoneHCID 4311764Sodium borohydrideHCID 10861106(S)-N-[2-[7-Allyl-5-bromo-2,3-dihydro-6-hydroxy-1H-inden-1-YL]ethyl]propanamide

Produkt 1

HCID 11068249HCID 11068249, VerbindungAusbeute 99 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

A solution of (S)-N-[2-(7-allyl-5-bromo-6-hydroxyindan-1-yl)ethyl]propionamide (588 mg, 1.67 mmol.) in methanol (30 mL) was cooled to about −70° C., to which was introduced ozone for 5 minutes. After confirming the disappearance of the starting material, an excess amount of powdery sodium borohydride (510 mg, 13.4 mmol.) was added to reaction mixture at about −70° C. to decompose ozonide. The reaction mixture was warmed to room temperature, which was neutralized with dilute hydrochloric acid, followed by extracting the organic matter with a mixture of ethyl acetate:butanol=1:1. The extract solution was dried over anhydrous magnesium sulfate, from which the solvent was distilled off under reduced pressure. The residue was then washed with diethyl ether to afford the title compound (yield 0.59 g, 99%).

Aufarbeitung

  1. extractionby extracting the organic matter
  2. additionwith a mixture of ethyl acetate
  3. dry with materialThe extract solution was dried over anhydrous magnesium sulfate, from which the solvent
  4. distillationwas distilled off under reduced pressure
  5. washThe residue was then washed with diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-75346678b8e54726aa47cecd5e175864
Quelldatensatz
uspto-grants-2001_04
Patentnummer
US06218429B1

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