Biotage^® PS-Benzaldehyde

Phenylhydrazine Scavenging: PS-Benzaldehyde resin (3 equivalents) in DCE was allowed to react with phenylhydrazine (1 equivalent) in the presence of a catalytic amount of glacial HOAc. The reaction was monitored by TLC and was complete after stirring for approximately 1 h at room temperature. The reaction may also be run without HOAc by heating for 1 h at 50 ˚C.

Scavenging Various Nucleophiles: PS-Benzaldehyde (3 equivalents) was added to a solution of the substrate in DCE along with a catalyst if necessary. The mixture was stirred for the specified time and temperature, and the filtrate was analyzed by TLC for disappearance of the substrate by comparison with standards.

Reductive Alkylation of Primary Amines.  A THF solution (0.50 M) of N-(3-aminopropyl)morpholine (1.2 mL, 0.60 mmol) was added to a THF solution (0.50 M) of 1,4-cyclohexanedione mono-ethylene ketal (1.0 mL, 0.50 mmol). MP-Triacetoxyborohydride (2.0 mmol/g, 0.625 g, 1.25 mmol) was then added and the mixture was agitated for 16 h at room temperature. When the reaction was complete, PS-Benzaldehyde (0.42 g, 0.5 mmol) and THF (2 mL) were added and the mixture was further agitated for 6 h. The resin was filtered and washed with THF (2 x 4 mL). The combined solution was concentrated to afford the product secondary amine as the acetate salt in high yield and purity.

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