Toluene → HCID 86607612, compound

HRID 2357622Notes

Reaction equation

HRID 2357622 reaction equation
[O:1]=[C:2]1[N:6]([C:7]([O:9][CH2:10][CH:11]=[CH2:12])=[O:8])[C@@H:5]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH2:4][CH2:3]1.[CH3:18][Al](C)C.C1(C)C=CC=CC=1>ClCCl>[OH:1][C:2]1([CH3:18])[N:6]([C:7]([O:9][CH2:10][CH:11]=[CH2:12])=[O:8])[C@@H:5]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH2:4][CH2:3]1

Participants

5

Reactant 3

HCID 1140TolueneHCID 16682925TrimethylaluminumHCID 86607613HCID 86607613, compound

Product 1

HCID 86607612HCID 86607612, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(R)-1-allyl 2-ethyl 5-oxopyrrolidine-1,2-dicarboxylate (9.1 g, 38 mmol) was dissolved in dichloromethane (100 mL) and cooled to 0° C. before trimethylaluminum −2 M in toluene (94 mL, 190 mmol) was added and the mixture was stirred at RT for 16 h. The reaction mixture was quenched with a minimal amount of ammonium chloride (saturated, aqueous) to form a white solid, which was filtered off to give the crude product. After purification by chromatography, the title compound was obtained. MS (ES+): 258 (M+H)+.

Workup

  1. additionwas added
  2. customThe reaction mixture was quenched with a minimal amount of ammonium chloride (saturated, aqueous)
  3. customto form a white solid, which
  4. filtrationwas filtered off
  5. customto give the crude product
  6. customAfter purification by chromatography

Sources & evidence

ORD record
ord-4048fa81cbd343d8b24f1c5efb4f596e
Source dataset
uspto-grants-2010_07
Patent number
US07759337B2

Reaction notes

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