Dimethyl Sulfide → Tert-butyl 4-hydroxy-2-(hydroxymethyl)pyrrolidine-1-carboxylate

関与物質

反応手順

To a stirred solution of N-Boc-hydroxyproline-methyl ester (343) (15 g, 65 mmol) in THF (70 mL) was added BH3.SMe2 (55 mL, 2.0 M in Et2O, 110 mmol). The solution was heated to reflux with stirring for four hours and reaction progress was monitored by TLC (5% MeOH/CHCl3, product had lower Rf than starting material, stained with K2MnO4). The heat was removed and the reaction was quenched by the slow addition of MeOH (40 mL). The resulting solution was heated to reflux again for 45 minutes, allowed to cool and concentrated to yield an oil that was purified by flash chromatography (1–15% MeOH in CHCl3) to give 12.68 g (˜90% yield) of the desired product (344).

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