Sodium periodate → HCID 86614493, compound

Participants

Reaction Steps

(2-Amino-3-nitro-6-vinyl-pyridin-4-yl)-(6-methyl-pyridin-3-ylmethyl)-carbamic acid ethyl ester (270 mgs/0.755 mmols) was dissolved in acetone (5 mls)/water (5 mls) and osmium tetroxide (2.5% wt in tBuOH) (0.10 mls/0.008 mmols) was added. Stirred for 5 mins to give brown solution then added sodium metaperiodate (500 mgs/3.47 mmols). Orange suspension stirred for 1 hour. Partitioned between EtOAc (100 mls) and sodium thiosulfate pentahydrate (20% wt in H2O) (50 mls). Organic collected, washed with brine, dried over Na2SO4, filtered and concentrated to a brown resin. Purification by column chromatography eluting with EtOAc gave the title compound (220 mgs) as a yellow oil.

Provenance & Evidence