Citric Acid → HCID 21478765, compound

HRID 2292487Notes

Reaction equation

HRID 2292487 reaction equation
P([O-])(O)(O)=O.[Na+].C(O)(=O)C[C:9]([CH2:14][C:15]([OH:17])=O)([C:11]([OH:13])=O)O.[CH2:20]([NH2:24])[CH2:21][CH2:22][CH3:23].[CH2:25]([C:32](O)=O)[C:26](CC(O)=O)=O.[OH-].[Na+].[OH-].[K+]>O.CO>[CH2:20]([N:24]1[CH:25]2[CH2:32][C:15](=[O:17])[CH2:14][CH:9]1[CH2:11][O:13][CH2:26]2)[CH2:21][CH2:22][CH3:23]

Participants

9

Reactant 6

HCID 311Citric AcidHCID 8007ButylamineHCID 14797Potassium HydroxideHCID 14798Sodium HydroxideHCID 68328Acetonedicarboxylic acidHCID 23672064Monosodium phosphate

Product 1

HCID 21478765HCID 21478765, compoundYield 88.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of sodium dihydrogenphospate (123.1 g) and citric acid (31.1 g) in water (3000 ml) were added in turn n-butylamine (35.5 g) and acetonedicarboxylic acid (77.0 g) and pH was adjusted to 4.6 with a 10% aqueous solution of sodium hydroxide. To the reaction solution was added dropwise at room temperature a solution of the crude aldehyde (23 g) in methanol (20 ml) and the mixture was stirred for 65 hours. Then, a 10% aqueous solution of potassium hydroxide (300 ml) was added to the reaction solution and extracted five times with chloroform. The combined organic layer was washed with a 10% aqueous solution of sodium hydroxide (200 ml), dried over potassium carbonate and the solvent was distilled off under reduced pressure. The residue was purified by a silica gel column chromatography (ethyl acetate) to give 9-(n-butyl)-3-oxa-9-azabicyclo[3.3.1]nonan-7-one (28.2 g).

Workup

  1. extractionextracted five times with chloroform
  2. washThe combined organic layer was washed with a 10% aqueous solution of sodium hydroxide (200 ml)
  3. dry with materialdried over potassium carbonate
  4. distillationthe solvent was distilled off under reduced pressure
  5. customThe residue was purified by a silica gel column chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-b54cc03a579e44e18e4cfa9773f27538
Source dataset
uspto-grants-1997_11
Patent number
US05684003

Reaction notes

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