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

HRID 2375337Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2375337
[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

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 17859820(6,7-Dihydro-5H-cyclopenta[b]pyrazin-6-yl)methanol

Produkt 1

HCID 86615340methanesulfonic acid 6,7-dihydro-5H-cyclopentapyrazin-6-ylmethyl esterAusbeute 88 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

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.

Aufarbeitung

  1. extractionextracted with dichloromethane
  2. customOrganic layer was dried
  3. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-b707544eeccc4e928401f4f48291c687
Quelldatensatz
uspto-grants-2008_12
Patentnummer
US07465737B2

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