Phthalimide → 1,1-dimethylethyl (1S,4S,6S)-4-[(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)methyl]-3-azabicyclo[4.1.0]heptane-3-carboxylate

Participants

Reaction Conditions

Reaction Steps

1,1-dimethylethyl (1S,4S,6S)-4-(hydroxymethyl)-3-azabicyclo[4.1.0]heptane-3-carboxylate D27 (310 mg), triphenylphosphine (1073 mg, 4.09 mmol) and phthalimide (502 mg, 3.41 mmol) were collected together and dissolved in THF (7 ml). The mixture was brought to 50° C. and then DIAD (0.796 ml, 4.09 mmol) was added dropwise. The mixture was stirred for 1 hour at 50° C. then 1 ml of water were added. Volatiles were removed in vacuum and the resulting crude was purified by silica gel chromatography (column size 10 g) using Cy/EtOAc=8:2 to Cy/EtOAc=5:5 to EtOAc 100%. It was recovered the title compound D28 (488 mg). UPLC: (Acid Final_QC): rt=0.80 minutes, peaks observed: 357 (M+1). C20H24N2O4 requires 356.

Provenance & Evidence