N-(Tert-butyl)-1-(fluoromethyl)cyclopropane-1-sulfonamide → 1-(Fluoromethyl)cyclopropane-1-sulfonamide

HRID 1852058Notes

Reaction equation

HRID 1852058 reaction equation
C([NH:5][S:6]([C:9]1([CH2:12][F:13])[CH2:11][CH2:10]1)(=[O:8])=[O:7])(C)(C)C>FC(F)(F)C(O)=O>[F:13][CH2:12][C:9]1([S:6]([NH2:5])(=[O:8])=[O:7])[CH2:11][CH2:10]1

Participants

3

Reactant 1

HCID 71005325N-(Tert-butyl)-1-(fluoromethyl)cyclopropane-1-sulfonamide

Product 1

HCID 717427101-(Fluoromethyl)cyclopropane-1-sulfonamide

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

To a round-bottom flask equipped with a stir bar was added N-(tert-butyl)-1-(fluoromethyl)cyclopropane-1-sulfonamide (5.66 g, 27.0 mmol) and trifluoroacetic acid (20 mL). The solution was stirred at room temperature for 18 h. The solution was concentrated in vacuo to afford a dark orange oil. The oil was treated with hexanes:EtOAc (4:1) upon which a solid crystallized. The crystals were collected via filtrated and residual solvent was removed in vacuo to afford 1-(fluoromethyl)cyclopropane-1-sulfonamide as a colorless, crystalline solid (3.5 g, 84%). 1H NMR (400 MHz, CDCl3) δ 4.79 (s, 1H), 4.67 (s, 1H), 3.28 (br. s., 2H), 1.63-1.56 (m, 2H), 1.16-1.10 (m, 2H).

Workup

  1. customTo a round-bottom flask equipped with a stir bar
  2. concentrationThe solution was concentrated in vacuo
  3. customto afford a dark orange oil
  4. customcrystallized
  5. customThe crystals were collected
  6. filtrationvia filtrated
  7. customresidual solvent was removed in vacuo

Sources & evidence

ORD record
ord-5ecb688fe3844c36b1030436a6331c8b
Source dataset
uspto-grants-2015_02
Patent number
US08957203B2

Reaction notes

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