Tributylstannane → HCID 59201456, compound

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Reaction Steps

A benzene solution of ((1R*,2R*)-2-bromocyclohexyloxy)(tert-butyl)dimethylsilane (17.8 g, 0.061 mol), 2-benzyloxycarbonylamino-acrylic acid methyl ester (8 g, 0.037 mol), AIBN (1.22 g, 0.019 mol) was heated to reflux. After 5 minutes, n-Bu3SnH (19.8 mL, 0.074 mol) was added. The resulting mixture was then stirred at reflux for 14 hours. Solvent was removed under reduced pressure, the residue was purified by column chromatography to give methyl 2-(benzyloxycarbonylamino)-3-((1S*,2R*)-2-(tert-butyldimethylsilyloxy)cyclohexyl)propanoate (6.5 g, 24%).

Provenance & Evidence