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

HRID 600295Notes

Reaction equation

HRID 600295 reaction equation
[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]

Participants

3

Reactant 1

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

Product 1

HCID 57999652(S)-2-amino-3-(4-iodophenyl)propanenitrileYield 87.9%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Conditions

Temperature
50 °C

Procedure

(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).

Workup

  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

Sources & evidence

ORD record
ord-33b7933a967f44bb89bb2a906656a63b
Source dataset
uspto-grants-2011_03
Patent number
US07902181B2

Reaction notes

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