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

HRID 22068

Reaction equation

HRID 22068 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>>[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

3

Reactant 2

HCID 5826DextroamphetamineHCID 67681966(S)-2-[(phenylisopropyl)amino]adenosine

Product 1

HCID 53927112(R)-2-[(1-Phenylpropyl)amino]adenosineYield 74.8%

Procedure

Combine the acetonide (2) (638 mg, 1.87 mmol) with D-(+)-amphetamine (4.5 g) and heat to 130° C. for 5 hours under nitrogen with stirring. After cooling, purify by flash chromatography (3% to 5% to 10% methanol/chloroform) followed by radial chromatography four times (2% to 4% to 6% to 8% to 10% methanol/chloroform, 4 mm plate) to provide the secondary amine (3) (0.56 g).

Workup

  1. temperatureAfter cooling
  2. custompurify by flash chromatography (3% to 5% to 10% methanol/chloroform)

Sources & evidence

ORD record
ord-303a333fba484a8fbb5194a1b76974ce
Source dataset
uspto-grants-1995_06
Patent number
US05426101

Linked notes

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