Hydroxyamine hydrochloride → Benzyl 3-(hydroxyimino)-2,3-dihydrospiro[indene-1,4'-piperidine]-1'-carboxylate

HRID 1695910Notes

Reaction equation

HRID 1695910 reaction equation
O=[C:2]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[C:4]2([CH2:9][CH2:8][N:7]([C:10]([O:12][CH2:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[O:11])[CH2:6][CH2:5]2)[CH2:3]1.[NH2:26][OH:27].Cl.CC([O-])=O.[Na+]>CCO>[OH:27][N:26]=[C:2]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[C:4]2([CH2:9][CH2:8][N:7]([C:10]([O:12][CH2:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[O:11])[CH2:6][CH2:5]2)[CH2:3]1

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 59433376Benzyl 3-oxo-2,3-dihydrospiro[indene-1,4'-piperidine]-1'-carboxylate

Product 1

HCID 72297710Benzyl 3-(hydroxyimino)-2,3-dihydrospiro[indene-1,4'-piperidine]-1'-carboxylateYield 99%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of benzyl 3-oxo-2,3-dihydrospiro[indene-1,4′-piperidine]-1′-carboxylate (3 g, 10.3 mmol) in EtOH (30 mL) containing NH2OH.HCl (1.43 g, 20.6 mmol) and NaOAc (1.52 g, 18.53 mmol) was heated under reflux for 1.5 h. The solvent was removed by evaporation and the residue was partitioned between CH2Cl2 and water. The organic phase was washed with brine, dried over Na2SO4, and concentrated to provide benzyl 3-(hydroxyimino)-2,3-dihydrospiro[indene-1,4′-piperidine]-1′-carboxylate (3.14 g, yield 99%), which was used directly in the next step.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 1.5 h
  3. customThe solvent was removed by evaporation
  4. customthe residue was partitioned between CH2Cl2 and water
  5. washThe organic phase was washed with brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-d3d924f4a4384b0195fad2a76365d25e
Source dataset
uspto-grants-2012_04
Patent number
US08163737B2

Reaction notes

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