Hydrochloric Acid → HCID 67032325, compound

Participants

Reaction Steps

To a solution of (S)-3-hydroxypyrrolidine (2.0 g, 22.9 mmol) in THF (40 mL) was added diisopropylethylamine (12.0 mL, 68.9 mmol) and 5-chlorosulfonyl-1-methyl-1H-pyrrole-2-carboxylic acid methyl ester (6.0 g, 25.3 mmol). The resulting solution was stirred at room temperature for 2 h. Upon completion, as determined by HPLC, the reaction was acidified with 3N HCl and partitioned between H2O (100 mL) and Ethyl acetate (100 mL). The layers were cut and the aqueous layer was extracted with Ethyl acetate (3×100 mL) and EtOAc:THF (1:1, 2×100 mL). The combined organic cuts were washed with a 50% aqueous brine solution (1×100 mL) and brine (1×100 mL), dried over Na2SO4, and concentrated under reduced pressure. Silica gel chromatography (Ethyl acetate:hexanes, 4:1) afforded 6.31 g (95%) of (S)-5-(3-hydroxy-pyrrolidine-1-sulfonyl)-1-methyl-1H-pyrrole-2-carboxylic acid methyl ester as a white solid, mp 108-109° C. 1H-NMR (400 MHz, CDCl3): δ 7.25 (d, 1H, J=2.4 Hz), 7.17 (d, 1H, J=2.4 Hz), 4.40 (brs, 1H), 3.96 (s, 3H), 3.83 (s, 3H), 3.33-3.40 (m, 3H), 3.20-3.23 (m, 1H), 1.93-2.02 (m, 1H), 1.82-1.89 (m, 1H), 1.79 (brs, 1H). Anal. Calcd. for C11H16N2O5S, C, 45.82; H, 5.59; N, 9.72; S, 11.12. Found: C, 45.92; H, 5.63; N, 9.61; S, 11.24.

Provenance & Evidence