Potassium Carbonate → trans-N-(4-hydroxytetrahydrofuran-3-yl)propane-2-sulfonamide

HRID 2060822Notes

Reaction equation

HRID 2060822 reaction equation
[CH:1]12[O:6][CH:5]1[CH2:4][O:3][CH2:2]2.[CH3:7][CH:8]([S:10]([NH2:13])(=[O:12])=[O:11])[CH3:9].C(=O)([O-])[O-].[K+].[K+]>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.O1CCOCC1>[OH:6][C@@H:5]1[CH2:4][O:3][CH2:2][C@H:1]1[NH:13][S:10]([CH:8]([CH3:9])[CH3:7])(=[O:12])=[O:11]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 675113,6-Dioxabicyclo[3.1.0]hexaneHCID 3549191Propane-2-sulfonamide

Product 1

HCID 67196247trans-N-(4-hydroxytetrahydrofuran-3-yl)propane-2-sulfonamide

Reagents, catalysts & solvents 2

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 312751,4-DioxaneSolvent

Procedure

3,6-Dioxabicyclo[3.1.0]hexane (1.90 g, 22.1 mmol), propane-2-sulfonamide (prepared according to the method of D. C. Johnson, II and T. S. Widlanski, Tetrahedron Letters 2004, 45, 8483-8487) (3.13 g, 25.4 mmol), potassium carbonate (584 mg, 4.23 mmol) and benzyltriethylammonium chloride (963 mg, 4.23 mmol) were suspended in dioxane (10 mL) and heated at reflux for 120 hours. The reaction was cooled to room temperature, filtered, concentrated in vacuo and purified by silica gel chromatography (Gradient: 40% to 80% ethyl acetate in heptane), to afford trans-N-(4-hydroxytetrahydrofuran-3-yl)propane-2-sulfonamide as a solid. Yield: 3.76 g, 18.0 mmol, 81%. 1H NMR (400 MHz, CDCl3) δ 1.38 (d, J=6.7 Hz, 3H), 1.40 (d, J=6.7 Hz, 3H) 2.91 (d, J=3.6 Hz, 1H), 3.22 (septet, J=6.8 Hz, 1H), 3.67-3.71 (m, 2H), 3.82 (m, 1H), 4.08-4.12 (m, 2H), 4.40 (m, 1H), 4.77 (d, J=8.4 Hz, 1H), 13C NMR (100 MHz, CDCl3) δ 16.44, 16.69, 54.18, 62.06, 71.47, 73.50, 77.64.

Workup

  1. temperatureheated
  2. temperatureat reflux for 120 hours
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. custompurified by silica gel chromatography (Gradient: 40% to 80% ethyl acetate in heptane)

Sources & evidence

ORD record
ord-d0d95c868c0441e3b1cd82fc3337832a
Source dataset
uspto-grants-2012_10
Patent number
US08278457B2

Reaction notes

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