4-Toluenesulfonyl chloride → (3S,4S)-3-azido-4-(toluene-4-sulfonyloxy)-pyrrolidine-1-carboxylic acid tert-butyl ester

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Reaction Steps

38.1 A solution of 530 mg (3S,4S)-3-azido-4-hydroxy-pyrrolidine-1-carboxylic acid tert-butyl ester (example 22.2) in 5 ml pyridine was cooled to 0° C. under an argon atmosphere and treated with 664 mg 4-toluenesulfonyl chloride. The mixture was slowly warmed to room temperature and stirred for 6 hrs. The pyridine was distilled off. The residue was taken up in CH2Cl2 and 10% aq. Na2CO3. The organic phase was washed with H2O and brine, dried over MgSO4, filtered and concentrated. The crude product was purified by column chromatography (silica gel, gradient: cyclohexane->cyclohexane/EtOAc 7:3) to give 628 mg (3S,4S)-3-azido-4-(toluene-4-sulfonyloxy)-pyrrolidine-1-carboxylic acid tert-butyl ester as viscous yellow oil. MS 405.3 ([M+Na]+)

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