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Diisobutylaluminum hydride → ((1r)-1-Phenylethyl){[3-(4-methoxyphenyl)-4-methylphenyl]methyl}amine

HRID 1072250
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1072250
[C:1]1([C@H:7]([NH:9][C:10]([C:12]2[CH:17]=[CH:16][C:15]([CH3:18])=[C:14]([C:19]3[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=3)[CH:13]=2)=O)[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CC(C[AlH]CC(C)C)C>C1(C)C=CC=CC=1>[C:1]1([C@H:7]([NH:9][CH2:10][C:12]2[CH:17]=[CH:16][C:15]([CH3:18])=[C:14]([C:19]3[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=3)[CH:13]=2)[CH3:8])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1.[C:1]1([C@H:7]([NH:9][CH2:10][C:12]2[CH:17]=[CH:16][C:15]([CH3:18])=[C:14]([C:19]3[CH:20]=[CH:21][C:22]([OH:25])=[CH:23][CH:24]=3)[CH:13]=2)[CH3:8])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 2

HCID 14487Diisobutylaluminum hydrideHCID 20803221n-((1r)-1-Phenylethyl)[3-(4-methoxyphenyl)-4-methylphenyl]carboxamide

Produkt 2

HCID 60010447((1r)-1-Phenylethyl){[3-(4-methoxyphenyl)-4-methylphenyl]methyl}amineHCID 600105454-(5-{[((1r)-1-Phenylethyl)amino]methyl}-2-methylphenyl)phenol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140
Toluene
Lösungsmittel

Versuchsvorschrift

To a solution of N-((1R)-1-phenylethyl)[3-(4-methoxyphenyl)-4-methylphenyl]carboxamide (0.12 g, 0.34 mmol) in 10 mL of toluene was added DIBAL-H (1 mL, 1.5 mmol). The reaction was then heated to 100 C. for 16 hours and cooled to RT. The reaction was quenched with 5 mL of 2N NaOH aq. soln. 100 mL of CH2Cl2 was used to extract the product. The organic phase was washed with 30 mL of brine, dried over Na2SO3 and concentrated in vacuo. The desired products were separated by silica gel column chromatography (30% to 60% EtOAc in hexane) provide ((1R)-1-phenylethyl){[3-(4-methoxyphenyl)-4-methylphenyl]methyl}amine and 4-(5-{[((1R)-1-phenylethyl)amino]methyl}-2-methylphenyl)phenol, which were treated with 1N HCl in Et2O separately to provide the HCl salts as white solids.

Aufarbeitung

  1. temperatureThe reaction was then heated to 100 C
  2. customThe reaction was quenched with 5 mL of 2N NaOH aq. soln
  3. extractionto extract the product
  4. washThe organic phase was washed with 30 mL of brine
  5. dry with materialdried over Na2SO3
  6. concentrationconcentrated in vacuo
  7. customThe desired products were separated by silica gel column chromatography (30% to 60% EtOAc in hexane)

Quellen und Nachweise

ORD-Eintrag
ord-a31d1a22c4ba4ce093da60519111af73
Quelldatensatz
uspto-grants-2005_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06908935B2

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