Sodium Hydroxide → 1-Amino-2-(4-(benzyloxy)phenyl)propan-2-ol

HRID 920534Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 920534
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15](=[O:17])[CH3:16])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[Si]([C:22]#[N:23])(C)C.[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+]>C1COCC1.[I-].[Zn+2].[I-].O>[NH2:23][CH2:22][C:15]([C:12]1[CH:13]=[CH:14][C:9]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[CH:10][CH:11]=1)([OH:17])[CH3:16]

Komponenten

8

Edukt 4

HCID 14798Sodium HydroxideHCID 82115Trimethylsilyl cyanideHCID 2452261-[4-(Benzyloxy)phenyl]ethan-1-oneHCID 21226445Aluminium lithium hydride

Produkt 1

HCID 150366201-Amino-2-(4-(benzyloxy)phenyl)propan-2-olAusbeute 86,2 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 9883512zinc(II)iodideKatalysatorHCID 962WaterLösungsmittel2×HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A mixture of 1-(4-benzyloxy-phenyl)-ethanone (18.50 g; 81.8 mmol), zinc iodide (0.52 g; 1.6 mmol), and trimethylsilyl cyanide (33.8 mL; 269.8 mmol) was stirred overnight at RT. Subsequently, the excess trimethylsilyl cyanide was removed in vacuo, and the residue dissolved in THF (100 mL). The resulting solution was added, dropwise, to a mixture of lithium aluminum hydride (12.7 g; 335.2 mmol) in THF (200 mL). The resulting mixture was heated under reflux for 2 h. Next, the mixture was cooled to 0° C. and treated successively with water (13 mL), 2M aqueous NaOH (26 mL), and water (13 mL). Thereafter the mixture was heated under reflux for 15 minutes, cooled again to RT, filtered over Kieselguhr, and concentrated in vacuo. The residue was purified by column chromatography (SiO2, MeOH) to afford 1-Amino-2-(4-benzyloxy-phenyl)-propan-2-ol (18.15 g).

Aufarbeitung

  1. customSubsequently, the excess trimethylsilyl cyanide was removed in vacuo
  2. dissolutionthe residue dissolved in THF (100 mL)
  3. additionThe resulting solution was added
  4. temperatureThe resulting mixture was heated
  5. temperatureunder reflux for 2 h
  6. temperatureNext, the mixture was cooled to 0° C.
  7. temperatureThereafter the mixture was heated
  8. temperatureunder reflux for 15 minutes
  9. temperaturecooled again to RT
  10. filtrationfiltered over Kieselguhr
  11. concentrationconcentrated in vacuo
  12. customThe residue was purified by column chromatography (SiO2, MeOH)

Quellen und Nachweise

ORD-Eintrag
ord-f15a7d614db342af9e344a5eaa448beb
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09273017B2

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