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

HRID 1441379노트

반응식

HRID 1441379 반응식
[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

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 887Methanol용매

실험 절차

(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.

후처리

  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

출처 및 근거

ORD 기록
ord-52aff16b10434bc88a358b970274a297
출처 데이터셋
uspto-grants-2010_02
특허 번호
US07655652B2

반응 노트

불러오는 중…