Iodide Ion → 1-(Benzenesulfonyl)-3-(SR)-iodomethyl-4-(SR)-phenylpyrrolidine

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Reaction Steps

A solution of 234 mg (0.51 mmol) of 1-(benzenesulfonyl)-3-(SR)-benzenesulfonyloxymethyl-4-(SR)-phenylpyrrolidine (from Example 1, Step D) and 1.1 g (7.7 mmol) of sodiuim iodide in 8 mL of acetone was heated at reflux for 20 h. The reaction mixture was partitioned between 50 mL of ether and 30 mL of H2O and the layers were separated. The organic layer was washed with 30 mL of sat'd NaCl and dried over MgSO4. The aqueous layers were combined and extracted with 30 mL of ether. The extract was dried; the organic layers were combined. and concentrated in vacuo. Flash chromatography on 25 g of silica gel using 3:2 v/v hexanes/ether as the eluant afforded 211 mg (96%) of the title compound as an oil. 1H NMR (500 MHz, CDCl3): δ2.43 (t, J=9.8, 1H), 2.64-2.74 (m, 2H), 3.30 (dd, J=2.5, 7.8, 1H), 3.47 (q, J=6.7, 1H), 3.67-3.74 (3H), 7.05-7.95 (1OH). Mass Spectrum (NH3-CI): m/z 428 (M+1).

Provenance & Evidence