Oxalic Acid → HCID 19908363, compound

HRID 1534887Notes

Reaction equation

HRID 1534887 reaction equation
[S:1]1[CH:5]=[CH:4][N:3]=[C:2]1/[CH:6]=[C:7]1\[CH2:8][N:9]2[CH2:14][CH2:13][CH:12]\1[CH2:11][CH2:10]2.[C:15]([OH:20])(=[O:19])[C:16]([OH:18])=[O:17]>CO.C(O)C.C(OCC)C.[Pt]>[C:15]([OH:20])(=[O:19])[C:16]([OH:18])=[O:17].[S:1]1[CH:5]=[CH:4][N:3]=[C:2]1[CH2:6][CH:7]1[CH:12]2[CH2:11][CH2:10][N:9]([CH2:14][CH2:13]2)[CH2:8]1

Participants

6

Reactant 2

HCID 971Oxalic AcidHCID 44209702HCID 44209702, compound

Product 1

HCID 19908363HCID 19908363, compoundYield 14%

Reagents, catalysts & solvents 3

HCID 23939PlatinumCatalystHCID 887MethanolSolventHCID 21585056Diethyl ether ethanolSolvent

Procedure

(±) Z 3((1,3-Thiazol-2-yl)methylene)-1-azabicyclo [2.2.2]octane (D34) (0.15g, 0.00073 moles) was hydrogenated in methanol (20ml) over a 5% platinum on sulphided carbon catalyst (0.6g) at 200 psi and 100° C. for 48h. The mixture was filtered through Kieselguhr and the filter pad washed with methanol (2×50ml). The combined filtrates were concentrated in vacuo and the residue subjected to column chromatography on TLC alumina eluting with 0.5% methanol/chloroform. This gave a white solid which was treated with anhydrous oxalic acid in ethanol/diethylether to give the title compound (E17) (0.03g, 14%) m.p. 126-130° C.

Workup

  1. filtrationThe mixture was filtered through Kieselguhr
  2. washthe filter pad washed with methanol (2×50ml)
  3. concentrationThe combined filtrates were concentrated in vacuo
  4. customThis gave a white solid which

Sources & evidence

ORD record
ord-c5e0e8d3cf3048c4aa3c0f05a02583c7
Source dataset
uspto-grants-1992_02
Patent number
US05091397

Reaction notes

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