2-Methylbutanal → (S)-3-ethyl-2-{[(S)-1-phenylethyl]amino}pentanenitrile

HRID 398292

Reaktionsgleichung

Reaktionsgleichung von HRID 398292
Cl.[CH3:2][C@H:3]([NH2:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[C-:11]#[N:12].[K+].[CH3:14][CH:15]([CH2:18][CH3:19])[CH:16]=O.[CH3:20]O.O>>[CH2:14]([CH:15]([CH2:18][CH3:19])[C@H:16]([NH:10][C@H:3]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[CH3:2])[C:11]#[N:12])[CH3:20]

Komponenten

5

Edukt 4

HCID 72842-MethylbutanalHCID 9032Potassium CyanideHCID 12236039Benzenemethanamine, alpha-methyl-, hydrochloride (1:1), (alphaS)-HCID 22242641Methanol--water (1/1)

Produkt 1

HCID 11644310(S)-3-ethyl-2-{[(S)-1-phenylethyl]amino}pentanenitrileAusbeute 74 %

Versuchsvorschrift

To (S)-(−)-α-methylbenzylamine hydrochloride salt (1.2 g, 7.6 mmol) in 80 mL of 1:1 MeOH/H2O was added potassium cyanide (0.5 g, 7.6 mmol) and 2-methylbutyraldehyde (0.94 mL, 7.6 mmol). A precipitate formed after 30 min. After 20 h, the suspension was filtered and washed with H2O to give (S)-3-ethyl-2-{[(S)-1-phenylethyl]amino}pentanenitrile as a white powder (1.29 g, 74%). Mass Spectrum (+ESI): 310 (M+H)+. Anal. Calc'd for C15H22N2: C, 78.21; H, 9.63; N, 12.16. Found: C, 77.90; H, 9.75; N, 12.32.

Aufarbeitung

  1. customA precipitate formed after 30 min
  2. filtrationthe suspension was filtered
  3. washwashed with H2O

Quellen und Nachweise

ORD-Eintrag
ord-01f0906b9e694e12a40c24a2b4e09498
Quelldatensatz
uspto-grants-2003_08
Patentnummer
US06610734B2

Verknüpfte Notizen

Wird geladen…