Di-p-toluoyltartaric acid → 8-Methoxy-2-aminotetralin

HRID 249460Notes

Reaction equation

HRID 249460 reaction equation
C1(C)C=CC(C(C(C(O)=O)(O)C(C(C2C=CC(C)=CC=2)=O)(O)C(O)=O)=O)=CC=1.[CH3:29][O:30][C:31]1[CH:32]=[CH:33][CH:34]=[C:35]2[C:40]=1[CH2:39][CH:38]([NH:41]CC1C=CC=CC=1)[CH2:37][CH2:36]2>>[CH3:29][O:30][C:31]1[CH:32]=[CH:33][CH:34]=[C:35]2[C:40]=1[CH2:39][CH:38]([NH2:41])[CH2:37][CH2:36]2

Participants

3

Reactant 2

HCID 12049127Di-p-toluoyltartaric acidHCID 12741413N-benzyl-8-methoxy-1,2,3,4-tetrahydronaphthalen-2-amine

Product 1

HCID 101979338-Methoxy-2-aminotetralin

Procedure

The resolution is performed on 8-methoxy-2-(benzylamino)tetralin with the aid of (-)-di-p-toluoyltartaric acid according to Karlsson, et al., Acta Chem. Scand., B 42, 231-236 (1988). The enantiomers of 8-methoxy-2-(benzylamino)tetralin are debenzylated, yielding the corresponding enantiomers of 8-methoxy-2-aminotetralin, i.e., R-(+)- and S-(-)-8-methoxy-2-aminotetralin.

Sources & evidence

ORD record
ord-e358c11ee4ab4afeb9c488842b9140a4
Source dataset
uspto-grants-1993_05
Patent number
US05214156

Reaction notes

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