Triphenylphosphine → dimethyl (S)-4-[1-(tert-butoxycarbonyl)-2-pyrrolidinylmethoxy]phthalate

Participants

Reaction Steps

To a stirred solution of dimethyl 4-hydroxyphthalate (3.00 g, 14.27 mmol), N-Boc-prolinol (2.87 g, 14.26 mmol), Ph3P (4.49 g, 17.12 mmol) in THF (50 mL) was added DIAD (3.40 mL, 17.27 mmol) at 0° C. Then the resulting mixture was heated under reflux overnight. The resulting mixture was evaporated and the residue was purified by column chromatography on silica-gel with n-hexane-EtOAc (3:1, v/v) as eluent to give 5.75 g (q.y.) dimethyl (S)-4-[1-(tert-butoxycarbonyl)-2-pyrrolidinyl methoxy]phthalate as an oil. 1H-NMR (CDCl3) δ1.47 (s, 9 H), 1.86-2.05 (m, 4 H), 3.36-3.40 (m, 2 H), 3.87 (m, 3 H), 3.91 (s, 3 H), 3.96-4.19 (m, 3 H), 7.03-7.24 (m, 2 H), 7.80 (m, 1H).

Provenance & Evidence