Ethyl Acetate → (+)-3-(2-Hydroxyethyl)-2,3-dihydrobenzofuran-7-yloxyacetic acid (-)-cis-2-benzylaminocyclohexanemethanol salt

HRID 2186741Notes

Reaction equation

HRID 2186741 reaction equation
[OH:1][CH2:2][CH2:3][CH:4]1[C:8]2[CH:9]=[CH:10][CH:11]=[C:12]([O:13][CH2:14][C:15]([OH:17])=[O:16])[C:7]=2[O:6][CH2:5]1.[CH2:18]([NH:25][C@H:26]1[CH2:31][CH2:30][CH2:29][CH2:28][C@H:27]1[CH2:32][OH:33])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C(OCC)(=O)C>C(O)C>[CH2:18]([NH:25][C@H:26]1[CH2:31][CH2:30][CH2:29][CH2:28][C@H:27]1[CH2:32][OH:33])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.[OH:1][CH2:2][CH2:3][CH:4]1[C:8]2[CH:9]=[CH:10][CH:11]=[C:12]([O:13][CH2:14][C:15]([OH:17])=[O:16])[C:7]=2[O:6][CH2:5]1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 853687(+)-cis-2-BenzylaminocyclohexanemethanolHCID 224489543-(2-Hydroxyethyl)-2,3-dihydrobenzofuran-7-yloxyacetic acid

Product 1

HCID 86758190(+)-3-(2-Hydroxyethyl)-2,3-dihydrobenzofuran-7-yloxyacetic acid (-)-cis-2-benzylaminocyclohexanemethanol saltYield 14%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3-(2-hydroxyethyl)-2,3-dihydrobenzofuran-7-yloxyacetic acid (2.91 g) was dissolved in ethanol (30 ml), and (−)-cis-2-benzylaminocyclohexanemethanol (1.88 g) was added to the resultant solution, followed by reflux and dissolution. Ethyl acetate (15 ml) was then added to the resultant solution, and the mixture was cooled to room temperature to obtain crystals. The thus-obtained crystals were filtered off, and then recrystallized 6 times from ethanol to obtain the object compound of 97%e.e (0.77 g, yield 14%).

Workup

  1. temperatureby reflux
  2. dissolutiondissolution
  3. customto obtain crystals
  4. filtrationThe thus-obtained crystals were filtered off
  5. customrecrystallized 6 times from ethanol
  6. customto obtain the object compound of 97%e.e (0.77 g, yield 14%)

Sources & evidence

ORD record
ord-596c7ce4b701481489afea09d1affffa
Source dataset
uspto-grants-2002_06
Patent number
US06407096B1

Reaction notes

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