2-(methylsulfonyl)pyridine synthesis

12synthesis methods

Product Name:2-(methylsulfonyl)pyridine
CAS Number:17075-14-8
Molecular formula:C6H7NO2S
Molecular Weight:157.19

21948-75-4 Synthesis

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Yield: 78 % ee ， 77%

Reaction Conditions:

with manganese(II) triflate;1-Adamantanecarboxylic acid;C₃₂H₃₈N₄O₂;dihydrogen peroxide in water;acetonitrile at -30 - 20; for 0.5 h;Inert atmosphere;Resolution of racemate;stereoselective reaction;Reagent/catalyst;

Steps:

General procedure for the oxidation kinetic resolution of racemic sulfoxides
General procedure: Mn(OTf)₂ (1.4 mg, 0.004 mmol) and L2 (2.0 mg, 0.004 mmol) were dissolved in acetonitrile, and the mixture was stirred at room temperature for 12 h. To the solution of manganese complex were added substrate (0.4 mmol), 0.2 equiv of aca (14.4 mg, 0.08 mmol), and 49 % aqeous hydrogen peroxide (56.5 mg, 0.4 mmol). Then decreased the temperature to -30 °C, and the reaction mixture was stirred at -30 °C for 0.5 h. The aqueous was separated, the organic layer was dried over MgSO₄, filtered, concentrated at reduced pressure. The product was purified by silica gel column chromatography to afford the corresponding sulfoxide and sulfone.

References:

Yang, Jinchuang;Wang, Lianyue;Lv, Ying;Li, Ning;An, Yue;Gao, Shuang [Tetrahedron Letters,2018,vol. 59,# 2,p. 156 - 159] Location in patent:supporting information