[CH2:1]([O:4][C:5]([N:7]1[CH2:11][C@H:10]([O:12][Si](C(C)(C)C)(C)C)[CH2:9][C@H:8]1[CH2:20][CH2:21][N:22]=[N+:23]=[N-:24])=[O:6])[CH:2]=[CH2:3].Cl.C(OCC)(=O)C.O>O1CCCC1>[CH2:1]([O:4][C:5]([N:7]1[CH2:11][C@H:10]([OH:12])[CH2:9][C@H:8]1[CH2:20][CH2:21][N:22]=[N+:23]=[N-:24])=[O:6])[CH:2]=[CH2:3]To a solution of (2R,4R)-1-allyloxycarbonyl-2-(2-azidoethyl)-4-(t-butyldimethylsilyloxy) pyrrolidine (29.7 g) in tetrahydrofuran was added dropwise 12N hydrochloric acid (15 ml) at ambient temperature. After stirring for 6 hours, the mixture was poured into a mixture of ethyl acetate and water. The organic layer was separated and the aqueous layer was extracted twice with ethyl acetate. The combined organic layer was washed with sat. sodium bicarbonate and brine, dried over magnesium sulfate and evaporated under reduced pressure to give (2R, 4R)-1-allyloxycarbonyl-2-(2-azidoethyl)-4-hydroxypyrrolidine (20.0 g).
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