Ammonium formate → (R)-1-(4-Amino-phenyl)-pyrrolidine-2-carboxylic acid cyclopropylamide

HRID 1441379ノート

反応式

HRID 1441379 の反応式
[CH:1]1([NH:4][C:5]([C@H:7]2[CH2:11][CH2:10][CH2:9][N:8]2[C:12]2[CH:17]=[CH:16][C:15]([N+:18]([O-])=O)=[CH:14][CH:13]=2)=[O:6])[CH2:3][CH2:2]1.C([O-])=O.[NH4+]>CO.[Pd]>[CH:1]1([NH:4][C:5]([C@H:7]2[CH2:11][CH2:10][CH2:9][N:8]2[C:12]2[CH:13]=[CH:14][C:15]([NH2:18])=[CH:16][CH:17]=2)=[O:6])[CH2:2][CH2:3]1

参加物

5

反応物 2

HCID 2723923Ammonium formateHCID 68685984(R)-1-(4-Nitro-phenyl)-pyrrolidine-2-carboxylic acid cyclopropylamide

生成物 1

HCID 68689756(R)-1-(4-Amino-phenyl)-pyrrolidine-2-carboxylic acid cyclopropylamide収率 96%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 887Methanol溶媒

実験手順

(R)-1-(4-Nitro-phenyl)-pyrrolidine-2-carboxylic acid cyclopropylamide (Method 60; 142 g, 5.1 mmol) was dissolved in MeOH (50 ml), to this was added ammonium formate (1.6 g, 26 mmol) and palladium (0.1 g). The reaction was heated at reflux for 60 minutes; reaction decolourised. MeOH was removed in vacuo and saturated ammonium chloride (50 ml) was added, the system was extracted with DCM (2×100 ml), dried and solvent removed in vacuo to yield the title compound as a brown gum (1.20 g, 96%). Product rapidly turned black on exposure to air. The product was used immediately without any purification; m/z 246.

後処理

  1. temperatureThe reaction was heated
  2. temperatureat reflux for 60 minutes
  3. customreaction decolourised
  4. customMeOH was removed in vacuo and saturated ammonium chloride (50 ml)
  5. additionwas added
  6. extractionthe system was extracted with DCM (2×100 ml)
  7. customdried
  8. customsolvent removed in vacuo

出典と根拠

ORDレコード
ord-52aff16b10434bc88a358b970274a297
出典データセット
uspto-grants-2010_02
特許番号
US07655652B2

反応ノート

読み込み中…