Thiophenol → (3R,6S)-3-(allyloxyamino)-6-((tert-butyldimethylsilyloxy)methyl)-1,2,3,6-tetrahydropyridine-4-carboxamide

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Reaction Steps

To a reddish-brown, stirred suspension of (3R,6S)-3-(N-(allyloxy)-2,4-dinitrophenylsulfonamido)-6-((tert-butyldimethylsilyloxy)methyl)-1,2,3,6-tetrahydropyridine-4-carboxamide (Intermediate 106, 1.1 g, 1.9 mmol) and cesium carbonate (3.1 g, 9.5 mmol) in THF (about 45 mL), at ambient temperature under a blanket of argon, was added benzenethiol (polymer-bound reagent, 1.55 mmol/g) (4.5 g, 7.0 mmol). This mixture was stirred overnight at ambient temperature. Analysis by LCMS in the morning indicated complete consumption of starting material, as did analysis by TLC (5% methanol in methylene chloride). The mixture was filtered and the filtered material was rinsed with THF until no material remained that was responsive to UV or I2 stain on a silica plate. The red-orange solution obtained was concentrated and redissolved in methylene chloride. Normal-phase chromatography (0-6% methanol in methylene chloride, 80-g, 25 min.) afforded the desired compound (510 mg, 80%, orange-brown solid).

Provenance & Evidence