Ammonium formate → methyl 3-[(2S)-2-aminopropyl]benzoate

HRID 64456ノート

反応式

HRID 64456 の反応式
C1([C@@H]([NH:9][C@@H:10]([CH3:22])[CH2:11][C:12]2[CH:13]=[C:14]([CH:19]=[CH:20][CH:21]=2)[C:15]([O:17][CH3:18])=[O:16])C)C=CC=CC=1.C([O-])=O.[NH4+]>C(O)C.[OH-].[C+4].[Pd+2].[OH-].[OH-].[OH-].[OH-].[OH-]>[NH2:9][C@@H:10]([CH3:22])[CH2:11][C:12]1[CH:13]=[C:14]([CH:19]=[CH:20][CH:21]=1)[C:15]([O:17][CH3:18])=[O:16]

参加物

5

反応物 2

HCID 2723923Ammonium formateHCID 86713469methyl 3-[(2S)-2-{[(1S)-1-phenylethyl]amino}propyl]benzoate

生成物 1

HCID 86713468methyl 3-[(2S)-2-aminopropyl]benzoate収率 98.9%

試薬・触媒・溶媒 2

HCID 178420936HCID 178420936、化合物触媒HCID 702Ethanol溶媒

反応条件

温度
80 °C

実験手順

To a solution of 280 mg of methyl 3-[(2S)-2-{[(1S)-1-phenylethyl]amino}propyl]benzoate in 6.8 ml of ethanol were added 30 mg of 20% palladium-carbon hydroxide (wet) and 320 mg of ammonium formate, followed by stirring at 80° C. for 4 hours. The reaction mixture was filtered over Celite and the solvent was then evaporated under reduced pressure. To the obtained residue were added a saturated aqueous sodium hydrogen carbonate solution and chloroform to carry out a layer separation operation, followed by drying over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to obtain 180 mg of methyl 3-[(2S)-2-aminopropyl]benzoate.

後処理

  1. filtrationThe reaction mixture was filtered over Celite
  2. customthe solvent was then evaporated under reduced pressure
  3. additionTo the obtained residue were added a saturated aqueous sodium hydrogen carbonate solution and chloroform
  4. customa layer separation operation
  5. dry with materialby drying over anhydrous magnesium sulfate
  6. customThe solvent was evaporated under reduced pressure

出典と根拠

ORDレコード
ord-6aa1473429484d83946237626c3c6865
出典データセット
uspto-grants-2016_09
特許番号
US09447090B2

反応ノート

読み込み中…