Potassium Carbonate → HCID 69470950, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of (2R,5S)-1-(4-chloro-benzenesulfonyl)-2-phenyl-5-trimethylsilanyloxymethyl-pyrrolidine (0.76 g, 1.8 mmol) in 15 mL of MeOH at 0° C. was added K2CO3 (15 mg, 0.11 mmol, catalyst). After stirring at 0° C. for 30 min, the reaction mixture was partitioned between EtOAc (50 mL) and saturated brine (50 mL). The organic phase was separated, dried (Na2SO4) and concentrated under vacuum to give 0.63 g (100%) of (2R,5S)-[1-(4-chloro-benzenesulfonyl)-5-phenyl-pyrrolidin-2-yl]-methanol as a yellow gum. 1H NMR (CDCl3, 300 MHz) δ 7.90 (1H, d), 7.60 (1H, d), 7.40 (5H, m), 4.87 (1H, t), 4.10–3.90 (3H, m), 2.90 (1H, m), 2.05 (2H, m), 1.85 (2H, m). HPLC analysis using an analytical chiracel OD column (hexane/isopropanol) showed an e.e. >99% for this compound (r.t. for (2R,5S)-eantiomer=9.9 min, r.t. for (2S,5R)-enantiomer=12.3 min).

Provenance & Evidence