C(OC([N:8]1[CH2:12][CH2:11][C@@H:10]([O:13]S(C)(=O)=O)[CH2:9]1)=O)(C)(C)C.[NH2:18][C:19]1[C:28]2[C:23](=[CH:24][C:25](O)=[CH:26][CH:27]=2)[CH:22]=[CH:21][N:20]=1.C([O-])([O-])=O.[K+].[K+].O>CN(C)C=O.CO.C(O)(=O)C>[NH:8]1[CH2:12][CH2:11][C@H:10]([O:13][C:25]2[CH:24]=[C:23]3[C:28](=[CH:27][CH:26]=2)[C:19]([NH2:18])=[N:20][CH:21]=[CH:22]3)[CH2:9]1
A solution of (R)-3-methanesulfonyloxypyrrolidine-1-carboxylic acid tert-butyl ester (2.95 g) in N, N-dimethylformamide (2 ml) was added dropwise to a stirred solution of 1-amino-6-hydroxyisoquinoline (1.2 g, 7.4 mmol) and K2CO3 (1.02 g, 7.4 mmol) in N, N-dimethylformamide (10 ml) at 100° C. The mixture was stirred for 1 h then cooled and water added. The mixture was acidified with glacial acetic acid then diluted with methanol. The mixture was loaded onto a pre-acidified SCX column using methanol and eluted with 2M ammonia in methanol to afford crude (S)-6-(pyrrolidin-3-yloxy)isoquinolin-1-ylamine, which was purified by flash chromatography on silica (eluent: 10% methanol in DCM with 1% ammonium hydroxide), El-MS: m/z=230.3 [M+H]+.
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