Benzoyl chloride → 1-Benzoyl-5-methoxypyrrolidin-2-one

HRID 1709181Notes

Reaction equation

HRID 1709181 reaction equation
C([Li])CCC.[CH3:6][O:7][CH:8]1[NH:12][C:11](=[O:13])[CH2:10][CH2:9]1.[C:14](Cl)(=[O:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>CCCCCC.O1CCCC1>[C:14]([N:12]1[CH:8]([O:7][CH3:6])[CH2:9][CH2:10][C:11]1=[O:13])(=[O:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

6

Reactant 3

HCID 7412Benzoyl chlorideHCID 181561PterolactamHCID 178418339Butyllithium

Product 1

HCID 30779301-Benzoyl-5-methoxypyrrolidin-2-oneYield 41.5%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

20.8 cm3 of a 1.5M solution of butyllithium in hexane is added at -70° C. to a solution of 3.8 g of 5-methoxy pyrrolidin-2-one in 160 cm3 of tetrahydrofuran. This temperature is maintained for 20 minutes, then 4.69 g of benzoyl chloride in solution in tetrahydrofuran is added. After allowing to return to ambient temperature, the mixture is concentrated to dryness and chromatographed on silica (eluent: hexane-ethyl acetate 1-1). 3 g of expected product is obtained. m.p. =92°-94° C. crystallized from isopropyl ether.

Workup

  1. temperatureThis temperature is maintained for 20 minutes
  2. customto return to ambient temperature
  3. concentrationthe mixture is concentrated to dryness
  4. customchromatographed on silica (eluent: hexane-ethyl acetate 1-1)

Sources & evidence

ORD record
ord-26bcabecb023441abb2136bba7e269c7
Source dataset
uspto-grants-1990_08
Patent number
US04948804

Reaction notes

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