Potassium Cyanide → (2S,3S)-3-(dibenzylamino)-2-hydroxypentanenitrile

HRID 1025298

Reaktionsgleichung

Reaktionsgleichung von HRID 1025298
[CH2:1]([N:8]([CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C@@H:9]([CH2:12][CH3:13])[CH:10]=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O1CCOCC1.S(=O)(O)[O-].[Na+].[C-:32]#[N:33].[K+]>O>[CH2:14]([N:8]([CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[C@@H:9]([CH2:12][CH3:13])[C@H:10]([OH:11])[C:32]#[N:33])[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Komponenten

6

Edukt 4

HCID 9032Potassium CyanideHCID 312751,4-DioxaneHCID 23665763Sodium BisulfiteHCID 57433110(S)-2-(dibenzylamino)butanal

Produkt 1

HCID 57872116(2S,3S)-3-(dibenzylamino)-2-hydroxypentanenitrile

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel3×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Under an atmosphere of argon, (S)-2-(dibenzylamino)butanal (8.55 g, 32.0 mmol, Eq: 1.00) was combined with dioxane (70 ml) to give a light yellow solution. The reaction was stirred for 10 min at 0° C. Then sodium bisulfite in water (40%, 26.5 ml) was added. The reaction was stirred for another 10 min at 0° C. Then potassium cyanide (8.33 g, 128 mmol, Eq: 4), diluted in water (35 ml) was added. The reaction was stirred overnight at RT. The reaction mixture was poured into water (75 ml) and extracted with ethyl acetate (2×75 ml). The organic layers were dried over Na2SO4 and concentrated in vacuo. The crude material was purified by flash chromatography (silica gel, 50 g, 0% to 40% ethyl acetate in heptane). The title compound was obtained as a light yellow oil (6.49 g, 68.9%, MS (m/e)=295.3 [M+H+]).

Aufarbeitung

  1. customto give a light yellow solution
  2. stirringThe reaction was stirred for another 10 min at 0° C
  3. additionwas added
  4. stirringThe reaction was stirred overnight at RT
  5. extractionextracted with ethyl acetate (2×75 ml)
  6. dry with materialThe organic layers were dried over Na2SO4
  7. concentrationconcentrated in vacuo
  8. customThe crude material was purified by flash chromatography (silica gel, 50 g, 0% to 40% ethyl acetate in heptane)

Quellen und Nachweise

ORD-Eintrag
ord-2442bd4f2357465c851495f8f548dba6
Quelldatensatz
uspto-grants-2014_05
Patentnummer
US08729061B2

Verknüpfte Notizen

Wird geladen…