1,8-Diazabicyclo(5.4.0)undec-7-ene → Ethyl 2-[(3R,3aR,6R,6aS)-6-[6-chloro-5-(4-phenylphenyl)-1-(2-trimethylsilyl-ethoxy-methyl)imidazo[4,5-b]pyridin-2-yl]oxy-2,3,3a,5,6,6a-hexahydrofuro[3,2-b]furan-3-yl]acetate

Participants

Reaction Steps

A mixture of 2-[[6-chloro-2-methylsulfonyl-5-(4-phenylphenyl)imidazo-[4,5-b]pyridin-1-yl]-methoxy]ethyl-trimethyl-silane (357 mg, 0.694 mmol), ethyl 2-[(3aR,6R,6aR)-6-hydroxy-2,3,3a,5,6,6a-hexahydrofuro[3,2-b]furan-3-yl]acetate (180 mg, 0.832 mmol), and DBU (150 uL, 0.995 mmol) in DMF (1.0 ml) was stirred at room temperature for 1 hour. The reaction mixture was diluted with EtOAc (200 ml), washed with water (5×30 ml), brine (1×10 mL), dried over MgSO4, filtered, and evaporated under reduced pressure to give the title compound as a mixture of isomers. C34H40ClN3O6Si 649.24 observed m/e: 650.28 (M+H)+ (Rt 1.09 and 1.17/2 min)

Provenance & Evidence