Oxalic Acid → HCID 86089278, compound

HRID 1869291Notes

Reaction equation

HRID 1869291 reaction equation
[CH2:1]([NH2:4])[CH2:2][CH3:3].[CH2:5]1[O:15][C:8]2([CH2:13][CH2:12][C:11](=O)[CH2:10][CH2:9]2)[O:7][CH2:6]1.[C:16]([OH:21])(=[O:20])[C:17]([OH:19])=[O:18]>C(O)C.C(O)(C)C.CO.[Pd]>[C:16]([OH:21])(=[O:20])[C:17]([OH:19])=[O:18].[CH2:5]1[O:15][C:8]2([CH2:13][CH2:12][CH:11]([NH:4][CH2:1][CH2:2][CH3:3])[CH2:10][CH2:9]2)[O:7][CH2:6]1

Participants

8

Reactant 3

HCID 971Oxalic AcidHCID 7852PropylamineHCID 5674151,4-Dioxaspiro[4.5]decan-8-one

Product 1

HCID 86089278HCID 86089278, compound

Reagents, catalysts & solvents 4

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 887MethanolSolventHCID 3776IsopropanolSolvent

Procedure

N-propylamine (88.5g, 123 mL, 1.5 mol) is added to a solution of 1,4-cyclohexanedione monoethylene ketal (156 g, 1 mol) in ethanol (780 mL). 5% Pd/C (50% water) is added to the mixture. The mixture is hydrogenated at 3 bar for several hours. Once the reaction has ended, the solvent is eliminated and the residue is dissolved in isopropanol (1.560 mL). A solution of oxalic acid (132 g, 1.5 mol) in MeOH (200 mL) is added dropwise to this solution. The suspension is stirred for 30 minutes and filtered on a plate, obtaining 274 g (95%).

Workup

  1. waitThe mixture is hydrogenated at 3 bar for several hours
  2. filtrationfiltered on a plate
  3. customobtaining 274 g (95%)

Sources & evidence

ORD record
ord-268aef26fce6423e972ea237fd4c5de1
Source dataset
uspto-grants-2009_12
Patent number
US07638542B2

Reaction notes

Loading…