Ethyl Acetate → HCID 59557026, compound

HRID 906948Notes

Reaction equation

HRID 906948 reaction equation
[Cl-].[Ce+3].[Cl-].[Cl-].C[Mg]Br.[CH2:8](OCC)C.[CH3:13][C@H:14]1[C:18](=[O:19])[CH2:17][CH2:16][N:15]1[C:20]([O:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[O:21].C(OCC)(=O)C>C1COCC1>[OH:19][C@@:18]1([CH3:8])[CH2:17][CH2:16][N:15]([C:20]([O:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[O:21])[C@H:14]1[CH3:13]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 24636Cerium(III) chlorideHCID 59556933benzyl (2S)-2-methyl-3-oxopyrrolidine-1-carboxylateHCID 178467822HCID 178467822, compound

Product 1

HCID 59557026HCID 59557026, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

A suspension (300 mL) of cerium chloride (47 g) in THF was cooled to −78° C., and 3 mol/L methylmagnesium bromide-diethyl ether solution (56 mL) was added dropwise while adjusting the temperature of the solution to not higher than −70° C. After the completion of the dropwise addition, the mixture was stirred at −78° C. for 30 min, and a solution (60 mL) of benzyl (2S)-2-methyl-3-oxopyrrolidine-1-carboxylate (18 g) in THF was added dropwise while adjusting the temperature of the solution to not higher than −70° C. The reaction mixture was warmed to 0° C. over 2 hr, ethyl acetate (1 L) was added, and the insoluble material was filtered off. Water was added to the filtrate and then the mixture was partitioned. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=9/1→1/1) to give the title compound as a colorless oil (yield: 16.2 g, yield: 84%).

Workup

  1. customhigher than −70° C
  2. additionAfter the completion of the dropwise addition
  3. customhigher than −70° C
  4. temperatureThe reaction mixture was warmed to 0° C. over 2 hr
  5. filtrationthe insoluble material was filtered off
  6. additionWater was added to the filtrate
  7. customthe mixture was partitioned
  8. washThe organic layer was washed with saturated brine
  9. dry with materialdried over anhydrous sodium sulfate
  10. concentrationconcentrated under reduced pressure
  11. customThe residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=9/1→1/1)

Sources & evidence

ORD record
ord-5019fcd52eeb4ddc8df167a380e9185c
Source dataset
uspto-grants-2011_09
Patent number
US08013008B2

Reaction notes

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