Carbon Tetrachloride → methyl 4-(cis-1-tert-butoxycarbonyl-4-chloro-(2S)-pyrrolidinyl)methoxybenzoate

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of methyl 4-(trans-1-tert-butoxycarbonyl-4-hydroxy-(2S)-pyrrolidinyl)methoxybenzoate (351 mg, 1.0 mmol) and Ph3P (393 mg, 1.5 mmol) in CHCl3 (5.0 ml) was added CCl4 (5.0 ml) at room temperature. The reaction mixture was stirred at 50° C. for 24 hr. The reaction mixture was concentrated in vacuo. The residue was purified by column chromatography on silica gel with n-hexane to n-hexane-EtOAc (4:1, v/v) as eluent to give methyl 4-(cis-1-tert-butoxycarbonyl-4-chloro-(2S)-pyrrolidinyl)methoxybenzoate (340 mg, 92%) as a pale yellow oil. 1H-NMR (CDCl3) δ1.48 (s, 9H), 2.38-2.65 (m, 2H), 3.50-3.60 (m, 1H), 3.88 (s, 3H), 3.89-4.05 (m, 1H), 4.26-4.41 (m, 4H), 6.95-6.97 (m, 2H), 7.98 (d, J=8.5 Hz, 2H).

Provenance & Evidence