Triethylamine → HCID 10018358, compound
Reaction equation
[OH:1][CH2:2][CH:3]1[CH2:7][N:6]([C:8]2[CH:13]=[CH:12][C:11]([CH:14]([CH3:16])[CH3:15])=[CH:10][CH:9]=2)[C:5](=[O:17])[CH2:4]1.C(N(CC)CC)C.[CH3:25][S:26](Cl)(=[O:28])=[O:27].C([O-])(O)=O.[Na+]>ClCCl>[CH:14]([C:11]1[CH:12]=[CH:13][C:8]([N:6]2[C:5](=[O:17])[CH2:4][CH:3]([CH2:2][O:1][S:26]([CH3:25])(=[O:28])=[O:27])[CH2:7]2)=[CH:9][CH:10]=1)([CH3:15])[CH3:16]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
A mixture of 4-hydroxymethyl-1-(4-isopropyl-phenyl)-pyrrolidin-2-one obtained in step 3 (0.5 g, 2.14 mmol), dichloromethane (8 ml) and triethyl amine (0.30 g, 3.0 mol) was cooled to 0° C. and stirred for 15 min at that temperature. Methane sulfonyl chloride (0.3 g, 2.56 mmol) was added to the mixture over a period of 5 min and the reaction mixture was stirred for 1.5 hrs at 10-15° C. To this reaction mixture saturated NaHCO3 solution (10 ml) was added and the organic layer was separated. The aqueous layer was extracted with dichloromethane (20 ml). The combined organic layer was washed with saturated brine solution, dried over Na2SO4 and evaporated to obtain methanesulfonic acid 1-(4-isopropyl-phenyl)-5-oxo-pyrrolidin-3-ylmethyl ester as a brown oil (0.6 g, 90%).
Workup
- stirringthe reaction mixture was stirred for 1.5 hrs at 10-15° C
- customthe organic layer was separated
- extractionThe aqueous layer was extracted with dichloromethane (20 ml)
- washThe combined organic layer was washed with saturated brine solution
- dry with materialdried over Na2SO4
- customevaporated
Sources & evidence
- ORD record
- ord-4cd50706afaf493a82b4ead3e50ebda0
- Source dataset
- uspto-grants-2012_08
- Patent number
- US08252797B2
Reaction notes
Loading…