Benzoyl chloride → 1-Benzoyl-5-(2,2-dimethylpropoxy)pyrrolidin-2-one

HRID 1709184Notes

Reaction equation

HRID 1709184 reaction equation
[CH2:1]([O:6][CH:7]1[NH:11][C:10](=[O:12])[CH2:9][CH2:8]1)[C:2]([CH3:5])([CH3:4])[CH3:3].C[Si]([N-][Si](C)(C)C)(C)C.[Na+].[C:23](Cl)(=[O:30])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>C(OCC)C>[C:23]([N:11]1[CH:7]([O:6][CH2:1][C:2]([CH3:5])([CH3:4])[CH3:3])[CH2:8][CH2:9][C:10]1=[O:12])(=[O:30])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 2724254Sodium bis(trimethylsilyl)amideHCID 15696561HCID 15696561, compound

Product 1

HCID 30779521-Benzoyl-5-(2,2-dimethylpropoxy)pyrrolidin-2-oneYield 41%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent3×

Conditions

Temperature
0 °C

Procedure

2.2 g of 5-neopentyloxy pyrrolidin-2-one in 30 cm3 of ethyl ether is added at ambient temperature to a solution of 2.6 g of sodium bis trimethylsilylamide in 160 cm3 of ethyl ether. After 30 minutes, the solution is cooled to 0° C. and 1.89 g of benzoyl chloride diluted with 20 cm3 of ethyl ether is added. After leaving the solution for 30 minutes at 0° C. then allowing to return to ambient temperature, and concentrating to dryness under reduced pressure, the residue is chromatographed on silica (eluent: hexane-ethyl acetate 7-3). After crystallization from ethanol, 1.45 g of expected product is obtained. m.p.=83°-85° C.

Workup

  1. additionis added
  2. customAfter leaving the solution for 30 minutes at 0° C.
  3. customto return to ambient temperature
  4. concentrationconcentrating to dryness under reduced pressure
  5. customthe residue is chromatographed on silica (eluent: hexane-ethyl acetate 7-3)
  6. customAfter crystallization from ethanol

Sources & evidence

ORD record
ord-86c6dbcc3b3d4dc0b26930321d8f1791
Source dataset
uspto-grants-1990_08
Patent number
US04948804

Reaction notes

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