Phenol → rac-benzyl (3R,4R)-3-hydroxy-4-phenoxypyrrolidine-1-carboxylate

HRID 971681Notes

Reaction equation

HRID 971681 reaction equation
[O:1]1[CH:6]2[CH:2]1[CH2:3][N:4]([C:7]([O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:8])[CH2:5]2.[C:17]1([OH:23])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[OH-].[Na+]>C(#N)C.O>[OH:1][C@H:2]1[C@H:6]([O:23][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:5][N:4]([C:7]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:8])[CH2:3]1

Participants

6

Reactant 3

HCID 996PhenolHCID 14798Sodium HydroxideHCID 22147363Benzyl 6-oxa-3-azabicyclo(3.1.0)hexane-3-carboxylate

Product 1

HCID 70546202rac-benzyl (3R,4R)-3-hydroxy-4-phenoxypyrrolidine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

21.9 g (0.1 mol) of 3,4-epoxy-1-carbobenzyloxy-pyrrolidine [S. Oida et al., Chem. Pharm. Bull., 18 (12), 2478 (1970)] are dissolved, together with 18.8 g (0.2 mol) of phenol and 100 ml of 2 N sodium hydroxide solution (0.2 mol) in 300 ml of acetonitrile. The reaction mixture is heated under reflux for 5 hours and after cooling is diluted with 600 ml of water and extracted by shaking with methylene chloride. The organic phase is washed with 2 N sodium hydroxide solution and then with water, dried over sodium sulphate and evaporated under a water pump vacuum and trans-3-hydroxy-4-phenoxy-1-carbobenzyloxy-pyrrolidine is obtained in the form of a pale yellow oil.

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureunder reflux for 5 hours
  3. temperatureafter cooling
  4. extractionextracted
  5. washThe organic phase is washed with 2 N sodium hydroxide solution
  6. dry with materialwith water, dried over sodium sulphate
  7. customevaporated under a water pump vacuum

Sources & evidence

ORD record
ord-ec6bb29f55204cb8a2fca8c569d52907
Source dataset
uspto-grants-1979_07
Patent number
US04160837

Reaction notes

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