Sodium Chloride → 1-(Benzenesulfonyl)-5-ethoxy-3-hydroxypyrrolidin-2-one

HRID 476599Notes

Reaction equation

HRID 476599 reaction equation
[CH2:1]([O:3][CH:4]1[N:8]([S:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)(=[O:11])=[O:10])[C:7](=[O:18])[CH2:6][CH2:5]1)[CH3:2].[Li].[Cl-].[NH4+].[Cl-].[Na+].[O:24]1CCCC1>CCCCCC.C1COCC1>[C:12]1([S:9]([N:8]2[CH:4]([O:3][CH2:1][CH3:2])[CH2:5][CH:6]([OH:24])[C:7]2=[O:18])(=[O:10])=[O:11])[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

7

Reactant 5

HCID 5234Sodium ChlorideHCID 8028TetrahydrofuranHCID 25517Ammonium ChlorideHCID 1830901-(Benzenesulfonyl)-5-ethoxypyrrolidin-2-oneHCID 3028194Lithium

Product 1

HCID 30781671-(Benzenesulfonyl)-5-ethoxy-3-hydroxypyrrolidin-2-one

Reagents, catalysts & solvents 1

HCID 21883165Tetrahydrofuran hexaneSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution of 10 g of 5-ethoxy-1-benzenesulfonylpyrrolidin-2-one in 300 cm3 of anhydrous tetrahydrofuran, cooled to -78° C., 0.037 moles of a solution of lithium bis-trimethylsylylamide in a mixture of hexane-tetrahydrofuran (1-1) is added drop by drop at a temperature of -78° C. This mixture is agitated for 1 hour at -78° C., then 14.55 g of 2-sulfonyloxaziridine is added. The mixture is then agitated at -78° C. for 2 hours, brought to -5° C., then cooled to -30° C., after which 130 cm3 of an aqueous solution of saturated ammonium chloride is added, while the temperature is maintained at approximately -30° C. The temperature is brought to 20° C., then 130 cm3 of an aqueous solution of saturated sodium chloride is added. The organic phase is separated and the aqueous phase is extracted with chloroform. The organic phases are combined, dried, and the solvent is evaporated under reduced pressure, then the residue is chromatographed on silica, using an ethyl acetate-hexane (2-1) mixture as eluent. The product is dissolved in isopropyl ether, and 250 g of the expected product is obtained, m.p. 108°-116° C. (mixture of cis and trans isomers in which the trans isomer predominates).

Workup

  1. additionis added drop by drop at a temperature of -78° C
  2. stirringThe mixture is then agitated at -78° C. for 2 hours
  3. custombrought to -5° C.
  4. temperaturecooled to -30° C.
  5. temperatureis maintained at approximately -30° C
  6. customis brought to 20° C.
  7. customThe organic phase is separated
  8. extractionthe aqueous phase is extracted with chloroform
  9. customdried
  10. customthe solvent is evaporated under reduced pressure
  11. customthe residue is chromatographed on silica
  12. dissolutionThe product is dissolved in isopropyl ether

Sources & evidence

ORD record
ord-369664ad82eb43268cfc6ec90814d09c
Source dataset
uspto-grants-1989_12
Patent number
US04885306

Reaction notes

Loading…