Hydrochloric Acid → 1-(Hept-6-enyl)cyclopropane-1-sulfonamide

HRID 2061420Notes

Reaction equation

HRID 2061420 reaction equation
Cl.O1CCOCC1.[CH2:8]([C:15]1([S:18]([NH:21]C(=O)OC(C)(C)C)(=[O:20])=[O:19])[CH2:17][CH2:16]1)[CH2:9][CH2:10][CH2:11][CH2:12][CH:13]=[CH2:14]>O>[CH2:8]([C:15]1([S:18]([NH2:21])(=[O:19])=[O:20])[CH2:17][CH2:16]1)[CH2:9][CH2:10][CH2:11][CH2:12][CH:13]=[CH2:14]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 59366234Tert-butyl 1-(hept-6-enyl)cyclopropylsulfonylcarbamate

Product 1

HCID 593662391-(Hept-6-enyl)cyclopropane-1-sulfonamideYield 92.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

4.0M HCl in dioxane (4.285 mL, 17.14 mmol) was added to tert-butyl 1-(hept-6-enyl)cyclopropylsulfonylcarbamate (544 mg, 1.714 mmol) and stirred at r.t. for 3 h. Poured into water, extracted with EtOAc. The organic layer was washed with brine, dried over MgSO4, filtered, concentrated in vacuo. The residue was purified by Biotage column, eluted with gradient 5%˜60% EtOAc-Hexane to afford the desired product 1-(hept-6-enyl)cyclopropane-1-sulfonamide (350 mg, 1.578 mmol, 92% yield) as a white solid. 1H NMR (400 MHz, CHLOROFORM-D) ppm 0.82-0.94 (m, 2 H) 1.28-1.53 (m, 8 H) 1.84-1.97 (m, 2 H) 2.06 (q, J=6.94 Hz, 2 H) 4.49 (b, NH2) 4.89-5.07 (m, 2 H) 5.70-5.90 (m, 1 H).

Workup

  1. extractionextracted with EtOAc
  2. washThe organic layer was washed with brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by Biotage column
  7. washeluted with gradient 5%˜60% EtOAc-Hexane

Sources & evidence

ORD record
ord-f058170d53ee493a8dcac81faf1f1344
Source dataset
uspto-grants-2012_10
Patent number
US08283310B2

Reaction notes

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