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

HRID 22065

Reaction equation

HRID 22065 reaction equation
[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

Participants

5

Reactant 4

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

Product 1

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

Conditions

Temperature
130 °C

Procedure

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).

Workup

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

Sources & evidence

ORD record
ord-91a42dcf5ab743dabf4e25dc19f9830e
Source dataset
uspto-grants-1995_06
Patent number
US05426101

Linked notes

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