trans-3-Hydroxy-4-phenoxy-1-(beta,beta,beta-trichloroethoxycarbonyl)-pyrrolidine → Rac-(3r,4r)-4-phenoxypyrrolidin-3-ol

HRID 2058962Notes

Reaction equation

HRID 2058962 reaction equation
[OH:1][C@H:2]1[C@H:6]([O:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:5][N:4](C(OCC(Cl)(Cl)Cl)=O)[CH2:3]1>C(O)(=O)C.[Zn]>[OH:1][C@H:2]1[C@H:6]([O:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:5][NH:4][CH2:3]1

Participants

4

Reactant 1

HCID 86736578trans-3-Hydroxy-4-phenoxy-1-(beta,beta,beta-trichloroethoxycarbonyl)-pyrrolidine

Product 1

HCID 13192209Rac-(3r,4r)-4-phenoxypyrrolidin-3-ol

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

1.77 g (0.005 mol) of the resulting trans-3-hydroxy-4-phenoxy-1-(β,β,β-trichloroethoxycarbonyl)-pyrrolidine are dissolved in 20 ml of 90% strength acetic acid and the solution is treated at 0° with 2 g of zinc dust in portions. The reaction mixture is then stirred at room temperature for one hour and filtered through a layer of diatomaceous earth and the filtrate is rendered alkaline with concentrated sodium hydroxide solution and extracted 3 times with ether. The organic phase is washed with water, dried over calcium chloride and evaporated under a water pump vacuum, and trans-3-hydroxy-4-phenoxy-pyrrolidine is obtained in the form of the crude base, which crystallises from methylene chloride/hexane; melting point 120°-122°. The neutral fumarate of this compound, which has a melting point of 144°-146°, is obtained by reaction with a solution of fumaric acid in methanol/ether.

Workup

  1. filtrationfiltered through a layer of diatomaceous earth
  2. extractionextracted 3 times with ether
  3. washThe organic phase is washed with water
  4. dry with materialdried over calcium chloride
  5. customevaporated under a water pump vacuum

Sources & evidence

ORD record
ord-7211221dd1f448eebcc7407909ab3cee
Source dataset
uspto-grants-1982_03
Patent number
US04320137

Reaction notes

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