Triethylamine → Methanesulphonic acid 3-(2-methanesulphonyloxy-ethyl)-2-oxo-piperidin-3-ylmethyl ester
Reaction equation
[OH:1][CH2:2][CH2:3][C:4]1([CH2:11][OH:12])[CH2:9][CH2:8][CH2:7][NH:6][C:5]1=[O:10].C(N(CC)CC)C.[CH3:20][S:21](Cl)(=[O:23])=[O:22].C(=O)([O-])O.[Na+]>ClCCl>[CH3:20][S:21]([O:1][CH2:2][CH2:3][C:4]1([CH2:11][O:12][S:21]([CH3:20])(=[O:23])=[O:22])[CH2:9][CH2:8][CH2:7][NH:6][C:5]1=[O:10])(=[O:23])=[O:22]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
A solution of 1 mmol of 3-(2-hydroxy-ethyl)-3-hydroxymethyl-piperidin-2-one in 3 ml of dichloromethane is admixed at 0° C. with 3 mmol of triethylamine, followed by 2.2 mmol of methanesulphonyl chloride. The reaction mixture is stirred at 0° C. for an hour and then at room temperature for an hour. The reaction mixture is poured into saturated aqueous sodium hydrogen carbonate solution and extracted with dichloromethane (2×). The combined organic extracts are washed with brine, dried with sodium sulphate and evaporated. From the residue the title compound is identified by means of flash chromatography (SiO2 60 F) on the basis of the Rf value.
Workup
- waitat room temperature for an hour
- extractionextracted with dichloromethane (2×)
- washThe combined organic extracts are washed with brine
- dry with materialdried with sodium sulphate
- customevaporated
Sources & evidence
- ORD record
- ord-6f2971aaad7c4c438394dbb3f32b718b
- Source dataset
- uspto-grants-2011_12
- Patent number
- US08071773B2
Reaction notes
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