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The chromatographic purification conditions were as follows: Column: Hipersep 600 LP with an internal diameter of 60 cm. Stationary phase: Merck flash silica (63-200 μm, 80 kg, Mobile phase: 4:1 heptane/ethyl acetate, with a flow rate of 3 L/min nitrogen pressure, UV detection wavelength: 335 nm. Polar impurities were removed in the first injection, and the fractions that contained early eluting impurities and desired product were concentrated. A solvent exchange into toluene was performed to give, after concentration, a final of 20 L. The column was back washed with 3 of acetone and, after re-equilibration with 4:1 heptane/ethyl acetate, the 20 L from the first injection was divided into two portions and passed through the column with an acetone back wash with re-equilibration in between
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At this point it is unknown whether this intermediate is present in solution as the aldehyde species or as a cyclic aminal. Additional studies with techniques such as ReactIR would be necessary to clarify this point
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