Tramadol → Desmetramadol

HRID 1742028

Reaction equation

HRID 1742028 reaction equation
[CH3:1][N:2]([CH2:4][C@@H:5]1[C@@:10]([OH:19])([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([O:17]C)[CH:12]=2)[CH2:9][CH2:8][CH2:7][CH2:6]1)[CH3:3].CN(C[C@H]1[C@](O)(C2C=CC=C(OC)C=2)CCCC1)C>CCO>[CH3:3][N:2]([CH2:4][C@@H:5]1[C@@:10]([OH:19])([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([OH:17])[CH:12]=2)[CH2:9][CH2:8][CH2:7][CH2:6]1)[CH3:1]

Participants

4

Reactant 2

HCID 33741TramadolHCID 667511(-)-(S,S)-trans-Tramadol

Product 1

HCID 9838803Desmetramadol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

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).

Sources & evidence

ORD record
ord-6fa8701eeca94b1196e05d5011e511a9
Source dataset
uspto-grants-1994_08
Patent number
US05336691

Linked notes

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