Cilobamine

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Cilobamine
Clinical data
ATC code
  • none
Identifiers
  • (2R,3R)-2-(3,4-Dichlorophenyl)-3-[(1-methylethyl)amino]bicyclo[2.2.2]octan-2-ol
JSmol)
  • Clc1ccc(cc1Cl)[C@@]3(O)[C@H](NC(C)C)C2CCC3CC2

Cilobamine is a drug which acts as a

norepinephrine-dopamine reuptake inhibitor (NDRI) and has stimulant and antidepressant effects.[1][2]

It can clearly be seen that the structure is based on dichloroisoprenaline that has been fused onto the bicycloalkane scaffold.

Synthesis

Patent:[3]

An intramolecular

Dieckmann cyclization on methyl 4-(2-methoxy-2-oxoethyl)cyclohexanecarboxylate [1401222-79-4] (3) with sodium hydride base gives reaction Methyl 3-oxobicyclo[2.2.2]octane-2-carboxylate [30144-30-0] (4). Treatment with sodium nitrite introduces an isonitroso group adjacent to the ketone, giving 3-Hydroxyiminobicyclo[2.2.2]octan-2-one, CID:131066320 (5). Addition of the aryl Grignard reagent, and reduction of the oxime gives CID:154108204
(6). A reductive amination of the primary amino group with acetone then completed the synthesis of cilobamine (7).

See also

References

  1. PMID 6724198
    .
  2. S2CID 145253439
    .
  3. ^ DE2003744 idem Jules Freedman, U.S. patent 3,651,142 (1970 to Colgate Palmolive Co).
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