Triethylamine → methanesulfonic acid 6,7-dihydro-5H-[1]pyrindin-6-ylmethyl ester
Reaction equation
[N:1]1[C:9]2[CH2:8][C@H:7]([CH2:10][OH:11])[CH2:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.[CH3:19][S:20](Cl)(=[O:22])=[O:21]>ClCCl.O>[N:1]1[C:9]2[CH2:8][CH:7]([CH2:10][O:11][S:20]([CH3:19])(=[O:22])=[O:21])[CH2:6][C:5]=2[CH:4]=[CH:3][CH:2]=1Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 0 °C
Procedure
To a solution of 895 mg (6 mmol) of (+)-(6R)-(6,7-dihydro-5H-[1]pyrindin-6-yl)-methanol in 50 ml of anhydrous dichloromethane was added at −15° C. 0.918 ml (6.6 mmol) of triethylamine and 0.465 ml (6 mmol) of methanesulfonyl chloride. The resulting mixture was stirred at 0° C. for 45 min. The mixture was then diluted with water and dichloromethane and extracted with dichloromethane. Organic layer was dried and evaporated to give 1.4 g (100%) of methanesulfonic acid 6,7-dihydro-5H-[1]pyrindin-6-ylmethyl ester.
Workup
- extractionextracted with dichloromethane
- customOrganic layer was dried
- customevaporated
Sources & evidence
- ORD record
- ord-1ba89299933a43f9b98d0c5e0985c791
- Source dataset
- uspto-grants-2008_12
- Patent number
- US07465737B2
Reaction notes
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