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

HRID 2360317Notes

Reaction equation

HRID 2360317 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, I I 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-17bd9a3eef834fc88a99e06f88faa5e0
Source dataset
uspto-grants-2014_04
Patent number
US08686043B2

Reaction notes

Loading…