Potassium hydroxy sulfite → HCID 57666543, compound

HRID 456010Notes

Reaction equation

[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([C:10]2[CH2:11][C:12]([CH3:19])([CH3:18])S[C:14]([CH3:17])([CH3:16])[CH:15]=2)=[N:8][CH:9]=1)([O-:3])=[O:2].O[O:21][S:22]([O-:24])=O.[K+]>CO.O>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([C:10]2[CH2:11][C:12]([CH3:19])([CH3:18])[S:22](=[O:24])(=[O:21])[C:14]([CH3:17])([CH3:16])[CH:15]=2)=[N:8][CH:9]=1)([O-:3])=[O:2]

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of 5-nitro-2-(2,2,6,6-tetramethyl-3,6-dihydro-2H-thiopyran-4-yl)-pyridine (0.300 g, 1.08 mmol, as prepared in the previous step) in MeOH (15 mL) was cooled to 0° C. and treated with oxone (984 mg, 3.23 mmol based on KHSO5 content) as a solution in water (1.5 mL). The ice bath was removed, and the mixture was allowed to stir at RT for 1 h. The mixture was diluted with water and extracted with CH2Cl2 (2×). The combined organic layers were dried over MgSO4 and concentrated in vacuo. The residue was purified on a 25-g Sepra Si 50 SPE column (Isco system: Flow rate=20 mL/min; Eluent=5% EtOAc-hexane for 0-3 min, then 5-15% EtOAc-hexane for 5-30 min) to afford the title product (322 mg, 96%) as an off-white solid. Mass spectrum (ESI, m/z): Calcd. for C14H18N2O4S, 311.1 (M+H), found 311.0.

Workup

customThe ice bath was removed
additionThe mixture was diluted with water
extractionextracted with CH2Cl2 (2×)
dry with materialThe combined organic layers were dried over MgSO4
concentrationconcentrated in vacuo
customThe residue was purified on a 25-g Sepra Si 50 SPE column (Isco system
waitEluent=5% EtOAc-hexane for 0-3 min

Sources & evidence

ORD record: ord-4cfeda1cf25b4f12ba73b1586f8c8621
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08497376B2

Reaction notes

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