Triethylamine → 5-Methanesulfonyloxymethyl-2-(3-methyl-butyryl)-pyridine

HRID 911717Notes

Reaction equation

[OH:1][CH2:2][C:3]1[CH:4]=[CH:5][C:6]([C:9](=[O:14])[CH2:10][CH:11]([CH3:13])[CH3:12])=[N:7][CH:8]=1.C(N(CC)CC)C.[CH3:22][S:23](Cl)(=[O:25])=[O:24]>ClCCl>[CH3:22][S:23]([O:1][CH2:2][C:3]1[CH:4]=[CH:5][C:6]([C:9](=[O:14])[CH2:10][CH:11]([CH3:12])[CH3:13])=[N:7][CH:8]=1)(=[O:25])=[O:24]

Participants

Conditions

Temperature: 0 °C

Procedure

Dissolve 5-hydroxymethyl-2-(3-methyl-butyryl)-pyridine (210 mg, 1.086 mmol) in dichloromethane (5 mL). Cool to 0° C. and add triethylamine (0.167 mL, 1.195 mmol) and methanesulfonyl chloride (0.093 mL, 1.195 mmol). Allow the mixture to warm to room temperature and stir for 2 h. Dilute the reaction mixture with dichloromethane and wash with saturated aqueous NaHCO3. Dry the organic phase over Na2SO4, filter and concentrate in vacuo to provide the title compound (256 mg, 87%). GC-MS m/z: 271

Workup

temperatureAllow the mixture to warm to room temperature
washwash with saturated aqueous NaHCO3
dry with materialDry the organic phase over Na2SO4
filtrationfilter
concentrationconcentrate in vacuo

Sources & evidence

ORD record: ord-8ca9c1eb03f64ec6b05e45aabb6f1235
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08022062B2

Reaction notes

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