Triethylamine → (S)-1-Benzyl-3-mesyloxypyrrolidine

Participants

Reaction Conditions

Reaction Steps

Methanesulfonyl chloride (15 mL, 0.19 mol) is added to a cooled (0° C.) solution of toluene (300 mL) containing (S)-1-benzylpyrrolidin-3-ol (24.5 g, 0.14 mol) and triethylamine (80 mL, 0.57 mol). The resulting mixture is stirred at 0° C. for 15 min, and allowed to warm to room temperature with stirring for 2 h. The mixture is quenched with a 5% aqueous solution of sodium bicarbonate (250 mL). The organic layer is washed with a 5% aqueous solution of sodium bicarbonate (2×250 mL), washed with water (1×250 mL), dried over magnesium sulfate, and concentrated under reduced pressure to give N (35.1 g, 99%) as an orange oil. 1H NMR (300 MHz, CDCl3): δ2.07 (m, 1H), 2.30 (m, 1H), 2.49 (m, 1H), 2.75-2.90 (m, 3H), 2.98 (s, 3H), 3.61 (d, J=13.0 Hz, 1H), 3.68 (d, J=13.0 Hz, 1H), 5.18 (m, 1H), 7.15-7.30 (m, 5H). LCMS m/z calcd for C12H17NO3S 255 ([M+]); found 256 ([M+H]+, 100%), 160 (40%).

Provenance & Evidence