Water → HCID 10798720, compound

Participants

Reaction Steps

At RT NaH (oil free, 12.5 mmol) is added to DMSO (15 mL). The mixture is treated portionwise with trimethylsulfoxonium iodide (12.7 mmol) and stirred for 30 min. A solution of (2R,5S)-2-Phenyl-3-oxa-1-azabicyclo[3.3.0]oct-6-en-8-on (4.97 mmol, J. Org. Chem. 1999, 64, 547-555) in DMSO (3.0 mL) is added and the mixture is stirred for 16 h. After cooling to 4° C. water and TBME (100 mL) are added, the layers are separated and the aq. layer is extracted with TBME (100 mL). The combined organic layers are concentrated in vacuo and the residue is purified by FC (heptane/EtOAc 1/1) to give the desired product as a pale yellow oil. LC-MS (basic): tR=0.77 min; [M+H]+=216.3.

Provenance & Evidence