Dabco → HCID 72485643, compound

Participants

Reaction Steps

To a mixture of rac-(4R,5S,6S)-1-benzyloxy-6-tert-butyldimethylsilyloxy-1-azaspiro[3.5]nona-8-ene-2,7-dione (3) (200 mg, 0.496 mmol) and trimethylsilyl cyanide (607 μl, 4.460 mmol) at room temperature (cooled with water bath) was slowly added DABCO (6 mg, 0.050 mmol). The mixture was stirred at room temperature for 14 h and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane-AcOEt, 5:1) to give rac-(4R,5S,6S,7S)-1-benzyloxy-6-tert-butyldimethylsilyloxy-7-cyano-5,7-bis(trimethylsilyloxy)-1-azaspiro[3.5]nona-8-ene-2-one (7) as a orange solid (254 mg, 89%).

Provenance & Evidence