Sulfamic Acid → 2-(1-Phenylcyclopentyl)acetic acid

HRID 1734906Notes

Reaction equation

HRID 1734906 reaction equation
S(=O)(=O)(O)N.Cl([O-])=[O:7].[Na+].[C:10]1([C:16]2([CH2:21][CH:22]=[O:23])[CH2:20][CH2:19][CH2:18][CH2:17]2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>C(O)(C)(C)C>[C:10]1([C:16]2([CH2:21][C:22]([OH:7])=[O:23])[CH2:20][CH2:19][CH2:18][CH2:17]2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 5987Sulfamic AcidHCID 199660432-(1-Phenylcyclopentyl)acetaldehydeHCID 23668197Sodium Chlorite

Product 1

HCID 199660452-(1-Phenylcyclopentyl)acetic acidYield 90%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

1 ml of an aqueous solution of 39 mg (0.402 mmol) of sulfamic acid and then 1 ml of an aqueous solution of 37.6 mg (0.416 mmol) of sodium chlorite were added dropwise to a solution of 58.4 mg (0.310 mmol) of 2-(1-phenylcyclopentyl)acetaldehyde [prepared as described in step (v) above] in 1 ml of t-butanol at room temperature, and the resulting mixture was stirred for 1 hour at room temperature, after which it was extracted with methylene chloride. The extract was washed with water and then dried over anhydrous sodium sulfate. The solvent was removed by distillation under reduced pressure, to give colorless crystals. These were recrystallized from a mixture of ethyl acetate and hexane, to give 57 mg (yield 90%) of the title compound as plate-like crystals.

Workup

  1. extractionafter which it was extracted with methylene chloride
  2. washThe extract was washed with water
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was removed by distillation under reduced pressure
  5. customto give colorless crystals
  6. customThese were recrystallized from a mixture of ethyl acetate and hexane

Sources & evidence

ORD record
ord-dae8a4fd4a224fbabd4a8045d3976a71
Source dataset
uspto-grants-1996_07
Patent number
US05534529

Reaction notes

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