Triethylamine → methanesulfonic acid 6,7-dihydro-5H-cyclopentapyrazin-6-ylmethyl ester

HRID 2375337Notes

Reaction equation

[N:1]1[C:6]2[CH2:7][CH:8]([CH2:10][OH:11])[CH2:9][C:5]=2[N: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:6]2[CH2:7][CH:8]([CH2:10][O:11][S:20]([CH3:19])(=[O:22])=[O:21])[CH2:9][C:5]=2[N:4]=[CH:3][CH:2]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 1.3 g (8.7 mmol) of (6,7-dihydro-5H-cyclopentapyrazin-6-yl)-methanol in 15 ml of anhydrous dichloromethane was added at −15° C. 1.33 ml (9.52 mmol) of triethylamine and 0.74 ml (9.52 mmol) of methanesulfonyl chloride. The resulting mixture was stirred at 0° C. for 1 h. The mixture was then diluted with water and dichloromethane and extracted with dichloromethane. Organic layer was dried and evaporated to give 1.73 g (88%) of methanesulfonic acid 6,7-dihydro-5H-cyclopentapyrazin-6-ylmethyl ester.

Workup

extractionextracted with dichloromethane
customOrganic layer was dried
customevaporated

Sources & evidence

ORD record: ord-b707544eeccc4e928401f4f48291c687
Source dataset: uspto-grants-2008_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07465737B2

Reaction notes

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