Didesmethylsibutramine → Didesmethylsibutramine, (+)-

HRID 455541Notes

Reaction equation

C(O)(=O)[C@H]([C@@H](C(O)=O)O)O.[Cl:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2([CH:22]([NH2:27])[CH2:23][CH:24]([CH3:26])[CH3:25])[CH2:21][CH2:20][CH2:19]2)=[CH:14][CH:13]=1>>[Cl:11][C:12]1[CH:13]=[CH:14][C:15]([C:18]2([C@H:22]([NH2:27])[CH2:23][CH:24]([CH3:25])[CH3:26])[CH2:21][CH2:20][CH2:19]2)=[CH:16][CH:17]=1

Participants

Reactant 2

HCID 134772Didesmethylsibutramine

HCID 439655D-Tartaric acid

Product 1

HCID 9900576Didesmethylsibutramine, (+)-

Procedure

As described above, D-(−)-tartaric acid was used to resolute racemic compound II to give another optical isomer (75.2% yield). This optical isomer were treated with alkaline to give free base (R)-1-[1-(4-chlorophenyl)cyclobutyl]-3-methylbutylamine (II-R) (optical purity 99.4%).

Workup

customto give another optical isomer (75.2% yield)
additionThis optical isomer were treated with alkaline

Sources & evidence

ORD record: ord-069e4819db2847d492317edf0ab902d5
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08497305B2

Reaction notes

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