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

HRID 1695910ノート

反応式

HRID 1695910 の反応式
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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-d3d924f4a4384b0195fad2a76365d25e
出典データセット
uspto-grants-2012_04
特許番号
US08163737B2

反応ノート

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