Acetonitrile → 1,5-Diazabicyclo(4.3.0)non-5-ene

Participants

Reaction Steps

1 g of tert-butyl (1R,3R,6S)-(7-oxa-bicyclo[4.1.0]hept-3-yl)-carbamate (Example 1 Step E), 1.56 g of triphenylmethanethiol, and 16.4 mL of acetonitrile were charged to a flask. To the mixture obtained 560 μL of DBN was added, and the mixture obtained was heated to 40° C. and stirred for 22.5 h. Upon completion of the reaction (TLC), the mixture obtained was cooled to rt, diluted with EtOAc, and washed with H2O and brine. The organic layer obtained was dried over MgSO4, concentrated in vacuo and the crude product obtained was subjected to column chromatography (eluent: cyclohexane/EtOAc 5:1). The required fractions were identified, combined and concentrated in vacuo.

Provenance & Evidence