N-bromobutanimide → (3S)-3-[(4-bromophenyl)amino]butanenitrile
Reaction equation
[C:1]1([NH:7][C@@H:8]([CH3:12])[CH2:9][C:10]#[N:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1C(=O)N([Br:20])C(=O)C1>CN(C)C=O>[Br:20][C:4]1[CH:5]=[CH:6][C:1]([NH:7][C@@H:8]([CH3:12])[CH2:9][C:10]#[N:11])=[CH:2][CH:3]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
(3S)-3-(phenylamino)butanenitrile (for a preparation see Intermediate 31) (11.3526 g, 70.9 mmol) was taken up in N,N-dimethylformamide (DMF) (200 mL) under nitrogen and cooled in an ice-bath. NBS (12.61 g, 70.9 mmol) was added and the reaction stirred. After 20 mins, the reaction was partitioned between EtOAc (1000 ml) and water (500 ml). The organic layer was washed with 2M NaOH ×2, water and brine (500 ml each) and then dried with Na2SO4, filtered and concentrated to yield the product as a cream solid (17.3 g).