Acetic Acid → HCID 54253000, compound

HRID 264603Notes

Reaction equation

HRID 264603 reaction equation
[CH2:1]([N:8]1[C@H:13]([CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:12][C:11](=[O:21])[CH:10](C(OC)=O)[C:9]1=[O:26])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)(=O)C.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1>[CH2:1]([N:8]1[C@H:13]([CH2:14][C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH2:12][C:11](=[O:21])[CH2:10][C:9]1=[O:26])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 10340Sodium CarbonateHCID 54410746HCID 54410746, compound

Product 1

HCID 54253000HCID 54253000, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 106.1 g (0.301 mol) of methyl (6R)-1,6-dibenzyl-2,4-dioxo3-piperidine carboxylate in 298 ml of toluene and 445 ml of 10% strength (vol/vol) acetic acid is heated at 80° for 21/2 hours. The reaction mixture is cooled to room temperature, neutralised by adding 48 g of solid sodium carbonate while cooling in ice-water, the phases are separated, and the aqueous phase is extracted once more with 300 ml of ethyl acetate. The combined organic phases are washed with water, then with brine dried over sodium sulfate and evaporated to dryness. The resulting oil is crystallised from ether, resulting in the title compound.

Workup

  1. customthe phases are separated
  2. extractionthe aqueous phase is extracted once more with 300 ml of ethyl acetate
  3. washThe combined organic phases are washed with water
  4. dry with materialwith brine dried over sodium sulfate
  5. customevaporated to dryness
  6. customThe resulting oil is crystallised from ether

Sources & evidence

ORD record
ord-d67f3548c2204eb6b27fe6326a62c9e1
Source dataset
uspto-grants-1997_07
Patent number
US05646144

Reaction notes

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