Methanesulfonyl chloride → 3-(R)-(1-BOC-2-(S)-pyrrolidinyl)-4-nitrobutanyl methylsulfonyl ether
Reaction equation
[C:1]([N:8]1[CH2:12][CH2:11][CH2:10][C@H:9]1[C@@H:13]([CH2:17][N+:18]([O-:20])=[O:19])[CH2:14][CH2:15][OH:16])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[CH3:21][S:22](Cl)(=[O:24])=[O:23]>C(Cl)Cl>[CH3:21][S:22]([O:16][CH2:15][CH2:14][C@@H:13]([C@@H:9]1[CH2:10][CH2:11][CH2:12][N:8]1[C:1]([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2])[CH2:17][N+:18]([O-:20])=[O:19])(=[O:24])=[O:23]Participants
4
Procedure
A 3.5 g sample of the alcohol from step 471a above was dissolved in 25 mL of methylene chloride and treated with methanesulfonyl chloride an TEA at 0° C. for 2 hours. The reaction mixture was washed with NaHCO3 solution and water, and the solvent was removed. The residue was chromatographed on silica gel to give 3 g of the title compound.