Benzyl Bromide → Tert-butyl-2-(benzhydrylideneamino)-3-phenylpropionate

HRID 384620

Reaktionsgleichung

Reaktionsgleichung von HRID 384620
[C:1]([O:5][C:6](=[O:22])[CH2:7][N:8]=[C:9]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)([CH3:4])([CH3:3])[CH3:2].[CH2:23](Br)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.[OH-].[K+]>C1(C)C=CC=CC=1>[C:1]([O:5][C:6](=[O:22])[CH:7]([N:8]=[C:9]([C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)[CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)([CH3:4])([CH3:2])[CH3:3]

Komponenten

5

Edukt 3

HCID 7498Benzyl BromideHCID 14797Potassium HydroxideHCID 688171N-(Diphenylmethylene)glycine tert-butyl ester

Produkt 1

HCID 11825189Tert-butyl-2-(benzhydrylideneamino)-3-phenylpropionateAusbeute 95 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

74 mg of tert-butyl(benzhydrylideneamino)acetate, 2.0 mg of an optically active quaternary ammonium salt compound (R,R)-(29), and 36 μl of benzylbromide were added to 2 ml of a toluene solvent at 0° C. 0.5 ml of 50% KOH aqueous solution was added dropwise to the resulting solution while stirring. The reaction solution was stirred for 8 hours at 0° C. and thereafter extracted by adding water and ether. The reaction product was purified by column chromatography (hexane:ether=15:1) to obtain targeted tert-butyl-2-(benzhydrylideneamino)-3-phenylpropionate (yield was 95%).

Aufarbeitung

  1. stirringThe reaction solution was stirred for 8 hours at 0° C.
  2. extractionextracted
  3. additionby adding water and ether
  4. customThe reaction product was purified by column chromatography (hexane:ether=15:1)

Quellen und Nachweise

ORD-Eintrag
ord-5bc1a4d5928243cf9bddbb16b3cb4e62
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08367820B2

Verknüpfte Notizen

Wird geladen…