Trifluoroacetic acid → (2S)-2-amino-3-(4-isopropoxyphenyl)propanenitrile

HRID 449481Notes

Reaction equation

HRID 449481 reaction equation
FC(F)(F)C(O)=O.[C:8]([C@@H:10]([NH:22]C(=O)OC(C)(C)C)[CH2:11][C:12]1[CH:17]=[CH:16][C:15]([O:18][CH:19]([CH3:21])[CH3:20])=[CH:14][CH:13]=1)#[N:9]>C(Cl)Cl>[NH2:22][C@@H:10]([CH2:11][C:12]1[CH:13]=[CH:14][C:15]([O:18][CH:19]([CH3:21])[CH3:20])=[CH:16][CH:17]=1)[C:8]#[N:9]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59496725(S)-tert-butyl 1-cyano-2-(4-isopropoxyphenyl)ethylcarbamate

Product 1

HCID 59496533(2S)-2-amino-3-(4-isopropoxyphenyl)propanenitrileYield 111.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (1 mL, 10 mmol) was added to a solution of the (S)-tert-butyl 1-cyano-2-(4-isopropoxyphenyl)ethylcarbamate (40 mg) in methylene chloride (2 mL). After stirring for 1 h., the reaction was concentrated under reduced pressure to give the crude product (2S)-2-amino-3-(4-isopropoxyphenyl)propanenitrile (30 mg, 90%).

Workup

  1. concentrationthe reaction was concentrated under reduced pressure

Sources & evidence

ORD record
ord-4982f29a1f2d473c921af8b9c687d731
Source dataset
uspto-grants-2013_07
Patent number
US08481732B2

Reaction notes

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