Reaction #1829210

ord-6fa8701eeca94b1196e05d5011e511a9

Reaction equation

COc1cccc([C@@]2(O)CCCC[C@@H]2CN(C)C)c1
(+)-tramadol
COc1cccc([C@]2(O)CCCC[C@H]2CN(C)C)c1
(-)-tramadol
→
CN(C)C[C@H]1CCCC[C@]1(O)c1cccc(O)c1
O-desmethyl tramadol

Reactants

COc1cccc([C@@]2(O)CCCC[C@@H]2CN(C)C)c1
(+)-tramadol
COc1cccc([C@]2(O)CCCC[C@H]2CN(C)C)c1
(-)-tramadol

Reagents

None

Solvents

CCO
EtOH

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Procedure

To prepare the (+) enantiomer of the title compound, the reaction was run under the same conditions except that (+)-tramadol as the free base was used instead of the (-)-tramadol to yield 2.8 g of the (+) enantiomer of O-desmethyl tramadol (mp. 242°-3° C.) [α]D25 =+32.2 (C=1, EtOH).

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US05336691uspto-grants-1994_08