Sodium borohydride → (2R,4R)-1-t-butoxycarbonyl-4-methanesulfonyloxypyrrolidine-2-methanol

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To a solution of (2R,4R)-1-t-butoxycarbonyl-4-methanesulfonyloxy-2-methoxycarbonylpyrrolidine (11.21 g: 34.4 mmole) in a mixture of tetrahydrofuran (34 ml) and ethanol (51 ml), sodium borohydride (5.21 g: 137.7 mmole) is added in a nitrogen atmosphere under ice cooling. The mixture is stirred for 75 minutes at room temperature to give (2R,4R)-1-t-butoxycarbonyl-4-methanesulfonyloxypyrrolidine-2-methanol (8.47 g). Yield: 83%. Colorless crystals. NMR δ(CDCl3) ppm: 1.48(s, 9H), 1.9 to 2.2(m, 1H), 2.3 to 2.5(m, 1H), 3.06 (s, 3H), 3.65(dd, J=11.2 Hz, J=4.0 Hz, 1H), 3.5 to 3.9(m, 2H), 3.84(dd, J=11.2 Hz, J=7.6 Hz, 1H), 4.1(m, 1H), 5.2(m, 1H). IR ν (KBr) cm-1 : 3490, 1688.

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