(S)-Tert-butyl (1-cyano-2-(4-iodophenyl)ethyl)carbamate → (S)-2-amino-3-(4-iodophenyl)propanenitrile

HRID 600295Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 600295
[C:1]([C@@H:3]([NH:12]C(=O)OC(C)(C)C)[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([I:11])=[CH:7][CH:6]=1)#[N:2]>C(O)=O>[NH2:12][C@@H:3]([CH2:4][C:5]1[CH:6]=[CH:7][C:8]([I:11])=[CH:9][CH:10]=1)[C:1]#[N:2]

Komponenten

3

Edukt 1

HCID 57999650(S)-Tert-butyl (1-cyano-2-(4-iodophenyl)ethyl)carbamate

Produkt 1

HCID 57999652(S)-2-amino-3-(4-iodophenyl)propanenitrileAusbeute 87,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 284Formic AcidLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

(S)-tert-Butyl 1-cyano-2-(4-iodophenyl)ethylcarbamate (1.4 g) and formic acid (3 mL) were combined and heated at 50° C. for 10 min. Solvent was removed in vacuo and crude material was loaded onto an SCX cartridge. Non-basic impurities were washed off with methanol, then product was eluted with 10% ammonia in methanol. Solvent was removed in vacuo to give (S)-2-amino-3-(4-iodophenyl)propanenitrile (0.900 g).

Aufarbeitung

  1. customSolvent was removed in vacuo and crude material
  2. washNon-basic impurities were washed off with methanol
  3. washproduct was eluted with 10% ammonia in methanol
  4. customSolvent was removed in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-33b7933a967f44bb89bb2a906656a63b
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07902181B2

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