N-Hydroxyphthalimide → 1,1-Dimethylethyl (2R)-2-((1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)oxy)propanoate

Participants

Reaction Conditions

Reaction Steps

To a slurry of N-hydroxyphthalimide (3.71 g, 22.1 mmol) and potassium carbonate (4.58 g, 33.1 mmol) in DMF (55 mL) was added (S)-tert-butyl 2-chloropropanoate (4.30 g, 24.3 mmol). After 72 h of stirring, the slurry was heated to 40° C. for an additional 16 h, at which point it was diluted with EtOAc/LiCl (5% aq) and the layers were separated. The aqueous layer was extracted with EtOAc (2×) and the combined organic layers were washed with LiCl (5% aq), brine, dried over Na2SO4 and concentrated in vacuo, affording the title compound (5.45 g, 85%) as an off-white solid. LCMS: Rt=0.88 min, m/z=313.9 (M+23) Method 2m_acidic.

Provenance & Evidence