(S)-tert-butyl 1-cyano-2-(3'-cyanobiphenyl-4-yl)ethylcarbamate → (S)-4'-(2-amino-2-cyanoethyl)biphenyl-3-carbonitrile
Reaction equation
[C:1]([C@@H:3]([NH:19]C(=O)OC(C)(C)C)[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([C:17]#[N:18])[CH:12]=2)=[CH:7][CH:6]=1)#[N:2]>C(O)=O>[NH2:19][C@H:3]([C:1]#[N:2])[CH2:4][C:5]1[CH:6]=[CH:7][C:8]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([C:17]#[N:18])[CH:12]=2)=[CH:9][CH:10]=1Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 50 °C
Procedure
A suspension of (S)-tert-butyl 1-cyano-2-(3′-cyanobiphenyl-4-yl)ethylcarbamate (8.4 g) in formic acid (100 mL) was stirred and heated to 50° C. for 10 min. The mixture was concentrated in vacuo. The crude material was dissolved in methanol (10 mL) and loaded on to an 50 g SCX cartridge. The impurities were washed through with methanol (100 mL) and discarded. The product was eluted with 1N methanolic ammonia (150 mL) and evaporated in vacuo. The residue was further purified by flash chromatography, eluting with ethyl acetate to afford (S)-4′-(2-amino-2-cyanoethyl)biphenyl-3-carbonitrile (3.32 g).
Workup
- concentrationThe mixture was concentrated in vacuo
- dissolutionThe crude material was dissolved in methanol (10 mL)
- washThe impurities were washed through with methanol (100 mL)
- washThe product was eluted with 1N methanolic ammonia (150 mL)
- customevaporated in vacuo
- customThe residue was further purified by flash chromatography
- washeluting with ethyl acetate
Sources & evidence
- ORD record
- ord-0ba66054e4ed49788bf885dbcc762547
- Source dataset
- uspto-grants-2011_03
- Patent number
- US07902181B2
Reaction notes
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