Trifluoroacetic acid → 5,6,7,8-Tetrahydroisoquinolin-3-amine
Reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]([NH2:11])[N:2]=1.C(O)(C(F)(F)F)=O>[Pt](=O)=O>[CH:1]1[C:10]2[CH2:9][CH2:8][CH2:7][CH2:6][C:5]=2[CH:4]=[C:3]([NH2:11])[N:2]=1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A mixture of isoquinolin-3-amine (239 mg, 1.66 mmol), platinum(IV)oxide (28 mg, 0.123 mmol), and TFA (6 mL) was hydrogenated in the Parr apparatus for 3 hrs. The reaction mixture was filtered with the aid of ethyl acetate. The filtrate was evaporated in vacuo and the residue was partitioned between 10% aqueous sodium carbonate and ethyl acetate. The layers were separated, the aqueous phase was washed again with ethyl acetate, and the combined organic layers were washed with brine and dried over magnesium sulfate. The drying agent was filtered off and the solvent evaporated. The material was purified by column chromatography in ethyl acetate to give 139.8 mg (57%) 5,6,7,8-tetrahydroisoquinolin-3-amine as a yellow-white solid. LCMS RT 0.75 min, MH+=149.1 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 7.78 (1H, s), 6.26 (1H, s), 4.29 (2H, br. s.), 2.64 (4H, ddd, J=10.6, 5.8, 5.5 Hz), 1.64-1.87 (4H, m).
Workup
- filtrationThe reaction mixture was filtered with the aid of ethyl acetate
- customThe filtrate was evaporated in vacuo
- customthe residue was partitioned between 10% aqueous sodium carbonate and ethyl acetate
- customThe layers were separated
- washthe aqueous phase was washed again with ethyl acetate
- washthe combined organic layers were washed with brine
- dry with materialdried over magnesium sulfate
- filtrationThe drying agent was filtered off
- customthe solvent evaporated
- customThe material was purified by column chromatography in ethyl acetate
Sources & evidence
- ORD record
- ord-e606d3e13f9749729e1e3385c0bb7781
- Source dataset
- uspto-grants-2012_11
- Patent number
- US08309577B2
Reaction notes
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