Oxalic Acid → HCID 86682347, compound

HRID 2281670Notes

Reaction equation

HRID 2281670 reaction equation
C([N:8]1[C:11]2([CH2:14][N:13]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:12]2)[CH2:10][CH2:9]1)C1C=CC=CC=1.[H][H].[C:24]([OH:29])(=[O:28])[C:25]([OH:27])=[O:26]>CO.C(OCC)C.C(O)C.[Pd]>[C:24]([O-:29])(=[O:28])[C:25]([O-:27])=[O:26].[C:18]([O:17][C:15]([N:13]1[CH2:12][C:11]2([NH2+:8][CH2:9][CH2:10]2)[CH2:14]1)=[O:16])([CH3:21])([CH3:19])[CH3:20].[C:18]([O:17][C:15]([N:13]1[CH2:12][C:11]2([NH2+:8][CH2:9][CH2:10]2)[CH2:14]1)=[O:16])([CH3:21])([CH3:19])[CH3:20]

Participants

8

Reactant 3

HCID 971Oxalic AcidHCID 86682346HCID 86682346, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 86682347HCID 86682347, compoundYield 78.2%

Reagents, catalysts & solvents 4

HCID 23938PalladiumCatalyst2×HCID 702EthanolSolventHCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Procedure

tert-Butyl 1-benzyl-1,6-diazaspiro[3.3]heptane-6-carboxylate (1.79 g, 6.21 mmol) was dissolved in methanol (33 mL), and Pd (10% on charcoal; 628 mg, 590 μmol) was added. A hydrogen atmosphere (balloon) was built up, and the mixture was stirred at ambient temperature for 24 h. Further Pd (10% on charcoal; 100 mg, 94 μmol, 0.015 equiv) was added and stirring under an hydrogen atmosphere was continued for another 24 h. The crude suspension was filtered over celite and the filter cake thoroughly washed with methanol, and the filtrate was concentrated under reduced pressure. To a solution of the residue in diethylether (140 mL) was added a solution of anhydrous oxalic acid (279 mg, 3.1 mmol) in ethanol (0.6 mL), upon which a precipitate formed immediately. The solid was filtered and dried under reduced pressure to give the title compound (1.18 g, 78%) as an amorphous colorless solid. MS (EI) m/e: 199.2 (M+H)+.

Workup

  1. stirringstirring under an hydrogen atmosphere
  2. waitwas continued for another 24 h
  3. filtrationThe crude suspension was filtered over celite
  4. washthe filter cake thoroughly washed with methanol
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customupon which a precipitate formed immediately
  7. filtrationThe solid was filtered
  8. customdried under reduced pressure

Sources & evidence

ORD record
ord-13c8e8fd6b2147dba489a42c2c67f1b3
Source dataset
uspto-grants-2015_09
Patent number
US09139593B2

Reaction notes

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