Hydroxyamine hydrochloride → (3aS,6aR)-2-butylhexahydrocyclopenta[c]pyrrol-5-one oxime

HRID 19732Notes

Reaction equation

HRID 19732 reaction equation
[CH2:1]([N:5]1[CH2:9][C@H:8]2[CH2:10][C:11](=O)[CH2:12][C@H:7]2[CH2:6]1)[CH2:2][CH2:3][CH3:4].Cl.[NH2:15][OH:16].C([O-])(=O)C.[Na+]>C(O)C.O>[CH2:1]([N:5]1[CH2:9][C@H:8]2[CH2:10][C:11](=[N:15][OH:16])[CH2:12][C@H:7]2[CH2:6]1)[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 68559398HCID 68559398, compound

Product 1

HCID 86611442(3aS,6aR)-2-butylhexahydrocyclopenta[c]pyrrol-5-one oxime

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A suspension of (3aS,6aR)-2-butylhexahydrocyclopenta[c]pyrrol-5-one (0.467 g, 2.58 mmol), hydroxylamine hydrochloride (0.430 g, 6.19 mmol) and sodium acetate (0.842 g, 6.19 mmol) in ethanol (21 ml) and water (7 ml) is heated to reflux for 1 hour. The ethanol is evaporated and the residue partitioned between saturated aqueous NaHCO3 and EtOAc. The organic phase is washed with brine, dried (MgSO4) and evaporated to afford (3aS,6aR)-2-butylhexahydrocyclopenta[c]pyrrol-5-one oxime, MH+197.

Workup

  1. temperatureis heated
  2. temperatureto reflux for 1 hour
  3. customThe ethanol is evaporated
  4. customthe residue partitioned between saturated aqueous NaHCO3 and EtOAc
  5. washThe organic phase is washed with brine
  6. dry with materialdried (MgSO4)
  7. customevaporated

Sources & evidence

ORD record
ord-b5a74cdf84d84e83bcf5cdc7da1404a2
Source dataset
uspto-grants-2010_06
Patent number
US07745462B2

Reaction notes

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