Sodium Bicarbonate → tert-butyl (1-(2-(7-methoxy-2-oxo-1,8-naphthyridin-1(2H)-yl)ethyl)piperidin-4-yl)carbamate

Participants

Reaction Steps

A solution of 7-(methyloxy)-1-(2-propen-1-yl)-1,8-naphthyridin-2(1H)-one (240 mg, 1.1 mmol) in 1,4-dioxane/water (12 ml/20 ml) was treated with osmium tetroxide solution (4% in water, 1 ml) followed by sodium periodate (2.1 g, 10 mmol). After 30 minutes more water (15 ml) was added. After a further 1 hour the mixture was diluted with an equal mixture of brine and extracted twice with ethyl acetate. The dried extracts were evaporated to give a yellow oil. This was dissolved in dichloromethane/methanol (6 ml/0.6 ml) and treated with 1,1-dimethylethyl 4-piperidinylcarbamate (240 mg, 1.2 mmol) then sodium triacetoxyborohydride (626 mg, 3 mmol). After 2 hours the mixture was treated with saturated aqueous sodium bicarbonate and dichloromethane. The organic extract was added to a silica column, eluting with 0-100% ethyl acetate in hexane then 0-20% methanol in ethyl acetate, affording a brown foam (320 mg, 72% over 2 steps).

Provenance & Evidence