water soluble additive such as NH4OAc, AcOH, etc. was added to
the reaction, the residue was partitioned between Et2O (10 mL)
and water (10 mL). The aqueous phase was extracted with Et2O
(10 mL ¥ 3), and then the combined organic phases were washed
with brine (10 mL), dried with anhydrous Na2SO4, filtered and
concentrated under reduced pressure.] The ratio of the primary
amine, secondary amine and tertiary amine was confirmed by 1H
NMR of the crude mixture in CDCl3. The crude mixture was
purified by flash silica gel column chromatography, if necessary.
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Acknowledgements
This work was partially supported by the Saijiro Endo Memorial
Foundation. The 10% Pd/C (K-type) was a gift from N.E.
Chemcat.
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