2,3-Dihydroxybutanedioic Acid → HCID 54080311, compound

HRID 1682549Notes

Reaction equation

HRID 1682549 reaction equation
[H-].[Na+].[OH:3][C:4]1[CH:5]=[C:6]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:7]=[CH:8][CH:9]=1.Br.[CH2:17]([O:19][C:20]([C@@H:22]1[CH2:27][CH2:26][CH2:25][N:24]([CH2:28][CH2:29]Br)[CH2:23]1)=[O:21])[CH3:18].C(O)(=O)C(C(C(O)=O)O)O>C1(C)C=CC=CC=1.C(OCC)(=O)C.O>[CH2:17]([O:19][C:20]([C@@H:22]1[CH2:27][CH2:26][CH2:25][N:24]([CH2:28][CH2:29][O:3][C:4]2[CH:9]=[CH:8][CH:7]=[C:6]([C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=3)[CH:5]=2)[CH2:23]1)=[O:21])[CH3:18]

Participants

8

Reactant 4

HCID 8752,3-Dihydroxybutanedioic AcidHCID 113813-PhenylphenolHCID 24758Sodium hydrideHCID 70009171(R)-1-(2-bromoethyl)nipecotic acid ethyl ester hydrobromide

Product 1

HCID 54080311HCID 54080311, compoundYield 73.2%

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Sodium hydride (0.46 g, 11.6 mmol, 60% oil dispersion) was added portionwise to a stirred solution of 3-hydroxybiphenyl (0.99 g, 5,8 mmol) in toluene (30 ml) placed under an atmosphere of nitrogen. The mixture was stirred for 30 minutes and (R)-1-(2-bromoethyl)-3-piperidinecarboxylic acid ethyl ester hydrobromide (2.0 g, 5.8 mmol, EP 374801) was added portionwise. The reaction mixture was stirred overnight at ambient temperature and water was added (50 ml). The phases were separated and the aqueous phase was extracted with toluene (20 ml). The solvent was evaporated in vacuo from the combined organic phases to give a residue which was dissolved in ethyl acetate (100 ml). Water (50 ml) was added and pH was adjusted to 4 with a 34% tartaric acid solution. The phases were separated and the organic phase extracted with 34% tartaric acid (2×5 ml). To the combined aqueous phases was added ethyl acetate (30 ml) and pH was adjusted to 7.5 with 2N sodium hydroxide. The organic phase was washed with brine (10 ml) and dried (Na2SO4). The solvent was evaporated in vacuo to give 1.5 g of (R)-1-(2-(3-Phenylphenoxy)ethyl)-3-piperidinecarboxylic acid ethyl ester as an oil.

Workup

  1. stirringThe reaction mixture was stirred overnight at ambient temperature
  2. customThe phases were separated
  3. extractionthe aqueous phase was extracted with toluene (20 ml)
  4. customThe solvent was evaporated in vacuo from the combined organic phases
  5. customto give a residue which
  6. customThe phases were separated
  7. extractionthe organic phase extracted with 34% tartaric acid (2×5 ml)
  8. additionTo the combined aqueous phases was added ethyl acetate (30 ml) and pH
  9. washThe organic phase was washed with brine (10 ml)
  10. dry with materialdried (Na2SO4)
  11. customThe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-4cf03998ae264bc2afc4a255cb3aefb1
Source dataset
uspto-grants-1997_06
Patent number
US05635518

Reaction notes

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