HCID 13534268, compound → HCID 13534269, compound

HRID 364947Notes

Reaction equation

HRID 364947 reaction equation
[O:1]=[C:2]1[N:9]2[C:5]([CH2:11][CH2:12][CH2:13][C:14]([O:16]CC3C=CC=CC=3)=[O:15])([CH2:6][CH2:7][C:8]2=[O:10])[CH2:4][CH2:3]1.[H][H]>O1CCCC1.[Pd]>[O:10]=[C:8]1[N:9]2[C:5]([CH2:11][CH2:12][CH2:13][C:14]([OH:16])=[O:15])([CH2:4][CH2:3][C:2]2=[O:1])[CH2:6][CH2:7]1

Participants

5

Reactant 2

HCID 13534268HCID 13534268, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 13534269HCID 13534269, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 1.0 g (0.0032 mole) tetrahydro-3,5-dioxo-1H-pyrrolizine-7a(5H)-butanoic acid, benzyl ester, prepared in Example I in tetrahydrofuran (30 ml) is treated with hydrogen in the presence of 0.1 g of a 20% Pd/C catalyst. The resulting solution is filtered to remove the catalyst and the product crystallizes upon concentration. Recrystallization from acetonitrile yields tetrahydro-3,5-dioxo-1H-pyrrolizine-7a(5H)-butanoic acid with a melting point of 178°-180° C.

Workup

  1. filtrationThe resulting solution is filtered
  2. customto remove the catalyst
  3. customthe product crystallizes upon concentration
  4. customRecrystallization from acetonitrile

Sources & evidence

ORD record
ord-fb4a88d43b4b4c41b36423d1d9223d23
Source dataset
uspto-grants-1986_08
Patent number
US04607043

Reaction notes

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