[CH2:1]([O:4][C:5]([N:7]1[CH2:11][C@H:10]([OH:12])[CH2:9][C@H:8]1[CH2:13][CH2:14][N:15]=[N+:16]=[N-:17])=[O:6])[CH:2]=[CH2:3].C(N(CC)CC)C.[CH3:25][S:26](Cl)(=[O:28])=[O:27].O>ClCCl>[CH2:1]([O:4][C:5]([N:7]1[CH2:11][C@H:10]([O:12][S:26]([CH3:25])(=[O:28])=[O:27])[CH2:9][C@H:8]1[CH2:13][CH2:14][N:15]=[N+:16]=[N-:17])=[O:6])[CH:2]=[CH2:3]
To a solution of (2R,4R)-1-allyloxycarbonyl-2-(2-azidoethyl)-4-hydroxypyrrolidine (20.0 g) and triethylamine (15.2 ml) in dichloromethane (300 ml) was added methanesulfonyl chloride (7.8 ml) under ice-cooling. After stirring for 1 hour, water was poured into the mixture. The organic layer was separated and the aqueous layer was extracted twice with dichloromethane. The combined organic layer was washed with 1N hydrochloric acid, sat. sodium bicarbonate, water and brine, dried over magnesium sulfate and evaporated under reduced pressure to give (2R,4R)-1-allyloxycarbonyl-2-(2-azidoethyl)-4-methanesulfonyloxypyrrolidine (15.3 g).
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