Water → Tert-butyl 3-(methanesulfonyloxy)pyrrolidine-1-carboxylate
Reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH:10]([OH:13])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:14][S:15](Cl)(=[O:17])=[O:16].O>N1C=CC=CC=1>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH:10]([O:13][S:15]([CH3:14])(=[O:17])=[O:16])[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -5 °C
Procedure
3-Hydroxy-pyrrolidine-1-carboxylic acid tert-butyl ester is dissolved in dry pyridine (20 ml) and cooled to −5° C. Methanesulphonyl chloride is added over a period of 10 minutes keeping the temperature between −5° C. and 0° C. after which the yellow solution is allowed to warm up to room temperature over a period of 30 minutes. Water (20 ml) is added and the mixture is then extracted using DCM (2×30 ml), the organic washings being combined and washed with 2N potassium hydrogen sulphate solution (2×30 ml). The organic phase is dried (using MgSO4), filtered and evaporated to give the title compound as a colourless oil.
Workup
- customthe temperature between −5° C. and 0° C.
- temperatureto warm up to room temperature over a period of 30 minutes
- extractionthe mixture is then extracted
- washwashed with 2N potassium hydrogen sulphate solution (2×30 ml)
- dry with materialThe organic phase is dried (using MgSO4)
- filtrationfiltered
- customevaporated
Sources & evidence
- ORD record
- ord-1f5d8513f5d3432ca28a00bbbe934eb6
- Source dataset
- uspto-grants-2010_07
- Patent number
- US07754758B2
Reaction notes
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