Formic Acid → Tert-butyl {[5-(benzyloxy)pyridin-3-yl](phenylsulfonyl)methyl}carbamate

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Reaction Steps

To 5-(Benzyloxy)pyridine-3-carbaldehyde (3.61 g, 16.9 mmol, Harrowven, D. C. et all Tetrahedron, 2001 57 p. 4447-4454) and benzenesulfinic acid sodium salt (2.7 g, 16.6 mmol) in THF (16.3 mL) was added water (36.3 mL), tert-butyl carbamate (1.94 g, 16.6 mmol) and formic acid (1.9 mL, 49 mmol). The mixture was stirred for 4 day and filtrated. The filtrate was stirred for 2 additional days and filtrated again. The formed precipitates were washed with water and triturated in hexane containing 9% dichloromethane. After filtration the solids were dried in vacuum to yield 3.17 g of tert-butyl {[5-(benzyloxy)pyridin-3-yl](phenylsulfonyl)methyl}carbamate.

Provenance & Evidence