Benzoyl chloride → 1-Benzoyl-5-(cyclopentyloxy)pyrrolidin-2-one

HRID 1709185Notes

Reaction equation

HRID 1709185 reaction equation
C([Li])CCC.[CH:6]1([O:11][CH:12]2[NH:16][C:15](=[O:17])[CH2:14][CH2:13]2)[CH2:10][CH2:9][CH2:8][CH2:7]1.[C:18](Cl)(=[O:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>CCCCCC.O1CCCC1>[C:18]([N:16]1[CH:12]([O:11][CH:6]2[CH2:7][CH2:8][CH2:9][CH2:10]2)[CH2:13][CH2:14][C:15]1=[O:17])(=[O:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

6

Reactant 3

HCID 7412Benzoyl chlorideHCID 15696562HCID 15696562, compoundHCID 178418339Butyllithium

Product 1

HCID 30779531-Benzoyl-5-(cyclopentyloxy)pyrrolidin-2-oneYield 70.2%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

11.8 cm3 of a 1.5M solution of butyllithium in hexane is added at -70° C. to a solution of 3 g of 5-cyclopentyloxy pyrrolidin-2-one in 140 cm3 of tetrahydrofuran. The mixture is maintained at this temperature for 20 minutes, then a solution of 2.49 g of benzoyl chloride in 20 cm3 of tetrahydrofuran is added. The whole is heated gently, then brought to dryness under reduced pressure. After chromatography on silica (eluent: hexane-ethyl acetate 7-3), 3.4 g of expected product is obtained.

Workup

  1. temperatureThe mixture is maintained at this temperature for 20 minutes
  2. temperatureThe whole is heated gently

Sources & evidence

ORD record
ord-ac952dd3491441108f679c808b985492
Source dataset
uspto-grants-1990_08
Patent number
US04948804

Reaction notes

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