Trifluoroacetic acid → (1R,2R)-N1-(1-(4-(Oxazol-2-yl)phenyl)piperidin-3-yl)cyclohexane-1,2-diamine
Reaction equation
[O:1]1[CH:5]=[CH:4][N:3]=[C:2]1[C:6]1[CH:11]=[CH:10][C:9]([N:12]2[CH2:17][CH2:16][CH2:15][CH:14]([NH:18][C@@H:19]3[CH2:24][CH2:23][CH2:22][CH2:21][C@H:20]3[NH:25]C(=O)OC(C)(C)C)[CH2:13]2)=[CH:8][CH:7]=1.O1C=CN=C1C1C=CC(N2CCCC2CN[C@@H]2CCCC[C@H]2NC(=O)OC(C)(C)C)=CC=1.FC(F)(F)C(O)=O>C(Cl)Cl>[O:1]1[CH:5]=[CH:4][N:3]=[C:2]1[C:6]1[CH:11]=[CH:10][C:9]([N:12]2[CH2:17][CH2:16][CH2:15][CH:14]([NH:18][C@@H:19]3[CH2:24][CH2:23][CH2:22][CH2:21][C@H:20]3[NH2:25])[CH2:13]2)=[CH:8][CH:7]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of tert-butyl (1R,2R)-2-(1-(4-(oxazol-2-yl)phenyl)piperidin-3-ylamino)cyclohexylcarbamate (32 mg, 0.073 mmol) and tert-butyl (1R,2R)-2-((1-(4-(oxazol-2-yl)phenyl)pyrrolidin-2-yl)methylamino)cyclohexylcarbamate (134.0 mg, 0.304 mmol) in CH2Cl2 (1.5 mL) was added trifluoroacetic acid (1.5 mL, 19.47 mmol). The reaction was stirred at rt for 1 h. After this time, LC/MS showed no starting material remained and the desired product formed. The reaction was concentrated, and the resulting residue was reconcentrated from CH2Cl2 (2×5 mL). The residue was dried under high vacuum for 1 h to afford the desired product (1R,2R)—N1-(1-(4-(oxazol-2-yl)phenyl)piperidin-3-yl)cyclohexane-1,2-diamine bis-trifluoroacetate (41 mg, 0.072 mmol, 99% yield) and (1R,2S)—N1-((1-(4-(oxazol-2-yl)phenyl)pyrrolidin-2-yl)methyl)cyclohexane-1,2-diamine bis-trifluoroacetate (35 mg, 0.073 mmol, 100% yield) as an oil.
Sources & evidence
- ORD record
- ord-a5c166f20bd84728b723d3604ad2a933
- Source dataset
- uspto-grants-2014_04
- Patent number
- US08710049B2
Reaction notes
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