Hexane → Benzyl 2-oxopyrrolidine-1-carboxylate

HRID 638834Notes

Reaction equation

HRID 638834 reaction equation
[NH:1]1[CH2:5][CH2:4][CH2:3][C:2]1=[O:6].CCCCCC.Cl[C:14]([O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:15]>C1COCC1>[C:14]([N:1]1[CH2:5][CH2:4][CH2:3][C:2]1=[O:6])([O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:15]

Participants

5

Reactant 3

HCID 8058HexaneHCID 10387Benzyl chloroformateHCID 120252-Pyrrolidone

Product 1

HCID 10932936Benzyl 2-oxopyrrolidine-1-carboxylateYield 87%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 2-pyrrolidinone (1.7 g, 21 mmol) in dry THF (25 mL), at −78° C., a 2.5 N solution of n-buthyllithium in n-hexane (8.4 mL, 21 mmol) is added. The mixture is stirred for 30′ and then a solution of benzyl chlorformate (3.03 mL, 21 mmol) in dry THF (30 mL) is added dropwise. The reaction mixture is stirred until the reaction is complete, quenched with saturated aqueous NH4Cl and ectracted with diethyl ether (3×). The combined organic phase is washed with brine and dried over anhydrous Na2SO4. Evaporation of the solvent gives 4 g (87%) of a colourless oil that is used without any further purification.

Workup

  1. additionis added dropwise
  2. customquenched with saturated aqueous NH4Cl
  3. washThe combined organic phase is washed with brine
  4. dry with materialdried over anhydrous Na2SO4
  5. customEvaporation of the solvent

Sources & evidence

ORD record
ord-5314c8d9463c4c4a959af046f097c045
Source dataset
uspto-grants-2010_04
Patent number
US07691818B2

Reaction notes

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