Triethylamine → methanesulfonic acid 6,7-dihydro-5H-[1]pyrindin-4-ylmethyl ester
Reaction equation
N1C2C[C@H:7]([CH2:10][OH:11])[CH2:6][C:5]=2[CH:4]=CC=1.C([N:14]([CH2:17][CH3:18])[CH2:15][CH3:16])C.[CH3:19][S:20](Cl)(=[O:22])=[O:21]>ClCCl.O>[N:14]1[C:15]2[CH2:16][CH2:4][CH2:5][C:6]=2[C:7]([CH2:10][O:11][S:20]([CH3:19])(=[O:22])=[O:21])=[CH:18][CH:17]=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-4-ylmethyl ester.
Workup
- extractionextracted with dichloromethane
- customOrganic layer was dried
- customevaporated
Sources & evidence
- ORD record
- ord-0230361b5fa940d8a8dab288f78fa3f7
- Source dataset
- uspto-grants-2007_06
- Patent number
- US07232827B2
Reaction notes
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