Dextroamphetamine → (R)-2-[(1-Phenylpropyl)amino]adenosine

HRID 22065

반응식

HRID 22065 반응식
[C:1]1([C:7]([NH:10][C:11]2[N:12]=[C:13]([NH2:29])[C:14]3[N:15]=[CH:16][N:17]([C:27]=3[N:28]=2)[C@H:18]2[O:26][C@H:23]([CH2:24][OH:25])[C@@H:21]([OH:22])[C@H:19]2[OH:20])([CH3:9])C)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:30][C@H](N)CC1C=CC=CC=1.C1([C@H](N)CC)C=CC=CC=1.C1([C@@H](N)CC)C=CC=CC=1>>[C:1]1([CH:7]([NH:10][C:11]2[N:12]=[C:13]([NH2:29])[C:14]3[N:15]=[CH:16][N:17]([C:27]=3[N:28]=2)[C@@H:18]2[O:26][C@H:23]([CH2:24][OH:25])[C@@H:21]([OH:22])[C@H:19]2[OH:20])[CH2:9][CH3:30])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

참가 물질

5

반응물 4

HCID 5826DextroamphetamineHCID 5324978(R)-1-PhenylpropylamineHCID 6993773(1S)-1-phenylpropan-1-amineHCID 67681966(S)-2-[(phenylisopropyl)amino]adenosine

생성물 1

HCID 53927112(R)-2-[(1-Phenylpropyl)amino]adenosine

반응 조건

온도
130 °C

실험 절차

In Scheme A, step b, the acetonide (2) is then treated with an appropriately substituted primary amine to provide the secondary amine of structure (3). More specifically, the acetonide (2) is combined with a large excess of an appropriately substituted primary amine, such as L-(-)-amphetamine, D-(+)-amphetamine, (R)-1-phenylpropylamine or (S)-1-phenylpropylamine, under an atmosphere of an inert gas such as nitrogen. The mixture is then heated to approximately 130° C. with stirring for approximately 3 to 6 hours. After cooling, the product can be isolated and purified by techniques well known to one skilled in the art. For example, the crude mixture can be directly purified by flash chromatography followed by radial chromatography using an appropriate eluent such as 3% to 6% methanol/chloroform to provide the secondary amine (3).

후처리

  1. temperatureAfter cooling
  2. customthe product can be isolated
  3. custompurified by techniques

출처 및 근거

ORD 기록
ord-91a42dcf5ab743dabf4e25dc19f9830e
출처 데이터셋
uspto-grants-1995_06
특허 번호
US05426101

연결된 노트

불러오는 중…