Ethyl Acetate → HCID 59557026, compound

HRID 1173585Notes

Reaction equation

HRID 1173585 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 of cerium chloride (47 g) in THF (300 mL) was cooled to −78° C., methylmagnesium bromide-diethyl ether solution (56 mL, 3 mol/L) was added dropwise while adjusting the solution temperature to −70° C. or below. After the completion of the dropwise addition, the mixture was stirred at −78° C. for 30 min, a solution of benzyl(2S)-2-methyl-3-oxopyrrolidine-1-carboxylate (18 g) in THF (60 mL) was added dropwise while adjusting the solution temperature to −70° C. or below. The reaction mixture was warmed to 0° C. over 2 hr, ethyl acetate (1 L) was added, and insoluble materials were filtered off. The filtrate was partitioned with water, and 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, 84%).

Workup

  1. customto −70° C. or below
  2. additionAfter the completion of the dropwise addition
  3. customto −70° C. or below
  4. temperatureThe reaction mixture was warmed to 0° C. over 2 hr
  5. filtrationinsoluble materials were filtered off
  6. customThe filtrate was partitioned with water
  7. washthe organic layer was washed with saturated brine
  8. dry with materialdried over anhydrous sodium sulfate
  9. concentrationconcentrated under reduced pressure
  10. customThe residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=9/1→1/1)

Sources & evidence

ORD record
ord-0b32a61df77c47d9915374284832dad3
Source dataset
uspto-grants-2010_11
Patent number
US07834051B2

Reaction notes

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