Methanesulfonyl chloride → 1-tert-Butyl 2-methyl (2S,4R)-4-((methanesulfonyl)oxy)pyrrolidine-1,2-dicarboxylate

HRID 1078714Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:17])[C@@H:4]1[CH2:8][C@@H:7]([OH:9])[CH2:6][N:5]1[C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11].[CH3:18][S:19](Cl)(=[O:21])=[O:20].C(=O)([O-])O.[Na+]>C(Cl)Cl.C(N(CC)CC)C>[CH3:1][O:2][C:3](=[O:17])[C@@H:4]1[CH2:8][C@@H:7]([O:9][S:19]([CH3:18])(=[O:21])=[O:20])[CH2:6][N:5]1[C:10]([O:12][C:13]([CH3:14])([CH3:16])[CH3:15])=[O:11]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of (2S,4R)-N-tert-butoxycarbonyl-4-hydroxyproline methyl ester (30.2 g, 123 mmol) in methylene chloride (300 ml) were dropwise added successively triethylamine (41.2 ml, 0.295 mmol) and methanesulfonyl chloride (17.1 ml, 0.221 mol) at 0° C. in a nitrogen atmosphere. The mixture was stirred at 0° C. for 2 h, and saturated aqueous sodium hydrogencarbonate was added. The mixture was extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride, and dried over anhydrous magnesium sulfate. The solvent was removed in vacuo. The residue was subjected to silica gel flash column chromatography (heptane-ethyl acetate=5:5) to give (2S,4R)-N-tert-butoxycarbonyl-4-methanesulfonyloxyproline methyl ester (39.5 g, yield: 99.1%).

Workup

extractionThe mixture was extracted with ethyl acetate
washThe organic layer was washed with saturated aqueous sodium chloride
dry with materialdried over anhydrous magnesium sulfate
customThe solvent was removed in vacuo

Sources & evidence

ORD record: ord-9b76289ec5214f2fb4ad40d37187c72b
Source dataset: uspto-grants-1996_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05550121

Reaction notes

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