Nitrogen → Tert-butyl 4-((4-((tert-butyldimethylsilyloxy) methyl)-2-methoxyphenylamino) methyl)phenylcarbamate

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Reaction Steps

To a solution of the amine 6 (91 mg, 0.34 mmol) and tert-butyl 4-formylphenylcarbamate (75 mg, 0.34 mmol) in dry dichloromethane (1.7 ml) was added a finely ground 1:1 mixture of MgSO4 and Na2SO4 (20 mg) and the mixture was stirred under N2 at room temperature for 3 days. The suspension was filtered through a 0.4 micron Whatman™ cartridge (GE Healthcare Biosciences, Pittsburgh, Pa.), the solvent was removed with a stream of dry N2 and the remaining red oil was dissolved in 1.2 ml dry THF and 0.2 ml anhydrous EtOH. Under vigorous stirring, sodium borohydride (14 mg, 0.37 mmol) was added and the mixture was stirred at room temperature for 30 min. Water (100 μl) was added and the solvent was stripped with a stream of N2. THF (1.5 ml) was added, the mixture was filtered through a 0.4 micron Whatman cartridge, dried with a stream of N2 and used crude in the next step.

Provenance & Evidence