Diisopropyl Ether → HCID 14989185, compound

HRID 484479Notes

Reaction equation

HRID 484479 reaction equation
Cl[C:2]([CH:4]1[CH2:8][CH2:7][N:6]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH2:5]1)=[O:3].S1C=CC=C1.O(C(C)C)C(C)C.[H][H]>CO.[Pd].CN(C)C(=O)C>[CH:2]([CH:4]1[CH2:8][CH2:7][N:6]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH2:5]1)=[O:3]

Participants

8

Reactant 4

HCID 7914Diisopropyl EtherHCID 8030ThiopheneHCID 14989184Ethyl 3-(chlorocarbonyl)pyrrolidine-1-carboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 14989185HCID 14989185, compoundYield 93%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 31374DimethylacetamideSolvent

Procedure

A mixture of 22 parts of ethyl 3-(chlorocarbonyl)-1-pyrrolidinecarboxylate, 36 parts of N,N-dimethylacetamide, 3 parts of a thiophene solution 4% in methanol and 210 parts of 2,2'-oxybispropane was hydrogenated at normal pressure and at room temperature with 3 parts of palladium-on-charcoal catalyst 10%. After the calculated amount of hydrogen was taken up, the catalyst was filtered off and the filtrate was evaporated, yielding 17 parts (93%) of ethyl 3-formyl-1-pyrrolidinecarboxylate as a residue (int 26).

Workup

  1. filtrationthe catalyst was filtered off
  2. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-c123c93bb3c34611a1748b2b3b8c54de
Source dataset
uspto-grants-1993_07
Patent number
US05231184

Reaction notes

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