Benzaldehyde → (3R,7aS)-3-Phenyltetrahydro-3H,5H-pyrrolo[1,2-c][1,3]oxazol-5-one

HRID 1099318Notes

Reaction equation

HRID 1099318 reaction equation
[OH:1][CH2:2][C@H:3]1[NH:7][C:6](=[O:8])[CH2:5][CH2:4]1.[CH:9](=O)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(=O)([O-])O.[Na+]>C1(C)C=CC=CC=1.O>[C:10]1([C@@H:9]2[N:7]3[C:6](=[O:8])[CH2:5][CH2:4][C@H:3]3[CH2:2][O:1]2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

7

Reactant 4

HCID 240BenzaldehydeHCID 6101p-Toluenesulfonic acidHCID 516892Sodium BicarbonateHCID 643511(S)-5-(Hydroxymethyl)-2-pyrrolidinone

Product 1

HCID 395160(3R,7aS)-3-Phenyltetrahydro-3H,5H-pyrrolo[1,2-c][1,3]oxazol-5-one

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 1140TolueneSolvent

Procedure

A suspension of 148.5 g of (S)-5-hydroxymethyl-pyrrolidin-2-one in 891 mL of toluene is treated with 172.1 mL of benzaldehyde at room temperature. p-Toluenesulphonic acid (2.94 g) is added and the reaction mixture stirred at reflux for 20 hours with azeotropic removal of water. The reaction mixture is treated with 500 mL of a 5% solution of sodium hydrogen carbonate in water. The organic layer is separated and washed once with 500 mL of a 40% solution of sodium bisulphite solution followed by 2×250 mL of water. The organic layer is dried with sodium sulphate, filtered and the solvent removed to give an oil. Fractional distillation in vacuum produces pure (3R,7aS)-3-phenyl-tetrahydro-pyrrolo[1,2-c]oxazol-5-one.

Workup

  1. customThe organic layer is separated
  2. washwashed once with 500 mL of a 40% solution of sodium bisulphite solution
  3. dry with materialThe organic layer is dried with sodium sulphate
  4. filtrationfiltered
  5. customthe solvent removed
  6. customto give an oil
  7. distillationFractional distillation in vacuum

Sources & evidence

ORD record
ord-11a33399651842a8bb24c59e0cc273fb
Source dataset
uspto-grants-2012_03
Patent number
US08143416B2

Reaction notes

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