4-Toluenesulfonyl chloride → (R)-tert-Butyl 2-((tosyloxy)methyl)pyrrolidine-1-carboxylate

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Reaction Steps

To a solution of (R)-2-hydroxymethyl-pyrrolidine-1-carboxylic acid tert-butyl ester (10.43 g, 52 mmol, 1 eq.) in pyridine (50 ml) was added p-toluenesulfonyl chloride (10.5 g, 55 mmol, 1.06 eq.) in one portion at 0° C. The resulting mixture was stirred at rt overnight. And then poured into ice-water (250 ml). The mixture was extracted with EtOAc (50 ml×3). The combined EtOAc layers was washed with water (50 ml) followed by 1N HCl (75 ml×4) and NaHCO3 aq. (75 ml), dried over MgSO4. Evaporation of solvent under reduced pressure gave the desired product as colorless oil (18 g, 100% yield); 1H NMR (400 MHz, CDCl3) δ 1.28-1.39 (m, 9H), 1.60-1.90 (m, 4H), 2.42 (s, 3H), 3.20 (m, 2H), 3.83 (m, 1H), 4.0 (m, 2H), 7.48 (d, J=8.0 Hz, 2H), 7.77 (d, J=8.0 Hz, 2H);

Provenance & Evidence