1,8-Diazabicyclo(5.4.0)undec-7-ene → Methyl 5,6-dihydro-2H-thiopyran-3-carboxylate

HRID 1053964Notes

Reaction equation

CS(O[CH:6]1[CH2:11][CH2:10][S:9][CH2:8][CH:7]1[C:12]([O:14][CH3:15])=[O:13])(=O)=O.C1CCN2C(=NCCC2)CC1>C(Cl)Cl>[S:9]1[CH2:10][CH2:11][CH:6]=[C:7]([C:12]([O:14][CH3:15])=[O:13])[CH2:8]1

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of methyl 4-((methylsulfonyl)oxy)tetrahydro-2H-thiopyran-3-carboxylate (4.33 g, 17.0 mmol) in DCM (170 mL) was added DBU (3.89 g, 25.5 mmol). The resulting mixture was refluxed at 50° C. for 30 minutes. The mixture was cooled to ambient temperature and washed with 1N aqueous HCl. The organic extract was washed with brine, dried over anhydrous Na2SO4, filtered, and concentrated in vacuo. The crude residue was purified by MPLC on silica gel (using a gradient elution of 0-45% EtOAc/hexanes) to afford the title compound. 1H NMR (500 MHz, CDCl3): δ 7.12-7.13 (m, 1H); 3.75 (s, 3H); 3.36 (q, J=2.2 Hz, 2H); 2.68 (t, J=5.8 Hz, 2H); 2.51-2.52 (m, 2H).

Workup

temperatureThe mixture was cooled to ambient temperature
washwashed with 1N aqueous HCl
extractionThe organic extract
washwas washed with brine
dry with materialdried over anhydrous Na2SO4
filtrationfiltered
concentrationconcentrated in vacuo
customThe crude residue was purified by MPLC on silica gel (
washa gradient elution of 0-45% EtOAc/hexanes)

Sources & evidence

ORD record: ord-e2b1eface1b9446091ccf96f4ec4bf9d
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09394282B2

Reaction notes

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