Ammonium formate → Methyl {3-[(2R)-2-aminopropyl]phenyl}acetate

HRID 494426ノート

反応式

HRID 494426 の反応式
C1([C@H]([NH:9][C@H:10]([CH3:23])[CH2:11][C:12]2[CH:13]=[C:14]([CH2:18][C:19]([O:21][CH3:22])=[O:20])[CH:15]=[CH:16][CH:17]=2)C)C=CC=CC=1.C([O-])=O.[NH4+]>C(O)C.[OH-].[OH-].[Pd+2]>[NH2:9][C@H:10]([CH3:23])[CH2:11][C:12]1[CH:13]=[C:14]([CH2:18][C:19]([O:21][CH3:22])=[O:20])[CH:15]=[CH:16][CH:17]=1

参加物

5

反応物 2

HCID 2723923Ammonium formateHCID 46938717methyl[3-((2R)-2-{[(1R)-1-phenyl-ethyl]-amino}-propyl)-phenyl]-acetate

生成物 1

HCID 46938716Methyl {3-[(2R)-2-aminopropyl]phenyl}acetate収率 100%

試薬・触媒・溶媒 2

HCID 9942167Palladium hydroxide触媒HCID 702Ethanol溶媒

実験手順

A solution of methyl [3-((2R)-2-{[(1R)-1-phenyl-ethyl]-amino}-propyl)-phenyl]-acetate (Preparation 89) (13.65 g, 40.9 mmol) and ammonium formate (12.9 g, 204 mmol) in ethanol (200 ml) was heated at reflux in the presence of 20% of palladium hydroxide on charcoal (Pd(OH)2/C, 1.36 g). After 3 hours the reaction mixture was cooled to room temperature, filtered through arbocel and the filtrate concentrated in vacuo. The residue was partitioned between dichloromethane (200 ml) and 880 ammonia (100 ml) and the organic phase separated. The aqueous phase was extracted with further dichlorormethane (3×100 ml) and the combined organic extracts washed with brine (100 ml), dried (sodium sulfate) and reduced in vacuo to give the title compound (8.48 g) as a pale yellow oil.

後処理

  1. filtrationfiltered through arbocel
  2. concentrationthe filtrate concentrated in vacuo
  3. customThe residue was partitioned between dichloromethane (200 ml) and 880 ammonia (100 ml)
  4. customthe organic phase separated
  5. extractionThe aqueous phase was extracted with further dichlorormethane (3×100 ml)
  6. washthe combined organic extracts washed with brine (100 ml)
  7. dry with materialdried (sodium sulfate)

出典と根拠

ORDレコード
ord-3d72c30d1d2745df839609238fe97019
出典データセット
uspto-grants-2009_05
特許番号
US07538141B2

反応ノート

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