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

HRID 22065

反応式

HRID 22065 の反応式
[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

参加物

5

反応物 4

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

生成物 1

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

反応条件

温度
130 °C

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-91a42dcf5ab743dabf4e25dc19f9830e
出典データセット
uspto-grants-1995_06
特許番号
US05426101

関連ノート

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