(+-)-Tetramisole → Levamisole

HRID 1855826Notes

Reaction equation

HRID 1855826 reaction equation
C1(P(CC2C(CP(C3C=CC=CC=3)C3C=CC=CC=3)C3CC2CC3)C2C=CC=CC=2)C=CC=CC=1.[CH:36]1[CH:37]=[CH:38][C:39]([CH:42]2[N:49]=[C:48]3[N:44]([CH2:45][CH2:46][S:47]3)[CH2:43]2)=[CH:40][CH:41]=1>[Rh].PP>[CH:36]1[CH:41]=[CH:40][C:39]([C@@H:42]2[N:49]=[C:48]3[N:44]([CH2:45][CH2:46][S:47]3)[CH2:43]2)=[CH:38][CH:37]=1

Participants

4

Reactant 2

HCID 3913(+-)-TetramisoleHCID 13296397HCID 13296397, compound

Product 1

HCID 26879Levamisole

Reagents, catalysts & solvents 1

HCID 18000278HCID 18000278, compoundCatalyst

Procedure

The utility of the compound of this invention: chiral-2,3-Bis(diphenylphosphinomethyl)bicyclo[2.2.1]heptane is as an intermediate in the manufacture of a chiral rhodium-diphosphine catalyst which is useful in the reduction of a tetramisole precursor to give a significant excess of the desired S-(-) isomer, levamisole. The chiral rhodium-diphosphine catalyst and the process of using the catalyst in the reduction of the tetramisole precursor is also novel.

Sources & evidence

ORD record
ord-d90867e7050940c189555f42febd71a3
Source dataset
uspto-grants-1980_08
Patent number
US04216331

Reaction notes

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