Methylparaben → HCID 11171084, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of cis-1-tert-butoxycarbonyl-4-dimethylamino-(2S)-hydroxymethylpyrrolidine (555 mg, 2.27 mmol), methyl 4-hydroxybenzoate (380 mg, 2.5 mmol), and Ph3P (1.07 g, 4.09 mmol) in THF (10 ml) was added DIAD (826 mg, 4.09 mmol) at 0° C. The reaction mixture was stirred at 70° C. for 18 hr. The mixture was concentrated in vacuo. The residue was purified by column chromatography on silica gel with n-hexane-EtOAc (1/2, v/v) MeOH—CH2Cl2(5/95, v/v) as eluent to give methyl 4cis-1-tert-butoxycarbonyl diethylamino-(2S)-pyrrolidinyl)methoxy benzoate (260 mg, 30%) as a pale yellow oil. 1H-NMR (CDCl3) δ1.45 (s, 9H), 1.70-1.90 (m, 1H), 2.26 (s, 6H), 2.33 (m, 1H), 2.57 (m, 1H), 3.06 (m, 1H) 3.85-4.23 (m, 4H), 388 (s, 3H), 6.93 (m, 2H), 7.95 (m, 2H).

Provenance & Evidence