Methanol → HCID 66936424, compound

HRID 1366528Notes

Reaction equation

HRID 1366528 reaction equation
[CH3:1][C:2]([C:19]([O:21]C)=O)([CH3:18])[N:3]([CH2:12][CH2:13][C:14]([O:16][CH3:17])=[O:15])[C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:5].CO.C[O-].[Na+]>C1(C)C=CC=CC=1>[CH3:18][C:2]1([CH3:1])[N:3]([C:4]([C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=2)=[O:5])[CH2:12][CH:13]([C:14]([O:16][CH3:17])=[O:15])[C:19]1=[O:21]

Participants

5

Reactant 3

HCID 887Methanol2×HCID 10942334Sodium MethoxideHCID 66936364HCID 66936364, compound

Product 1

HCID 66936424HCID 66936424, compoundYield 86.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of methyl 2-methyl-N-[3-(methyloxy)-3-oxopropyl]-N-(phenylcarbonyl)alaninate (3.5589 g, 11.58 mmol) in toluene (115 mL) was added MeOH (0.94 mL, 23.21 mmol), and NaOMe (1.25 g, 23.14 mmol). The mixture was heated at 60° C. and stirred for 2 h. An additional portion of MeOH (10 mL) was added, and the mixture was stirred for an additional 2 h at 60° C. The mixture was then concentrated in vacuo, and the residue was partitioned between DCM (200 mL) and 1 N aq. HCl (100 mL). The organic phase was dried over anhydrous MgSO4, filtered, and concentrated in vacuo to provide crude methyl 5,5-dimethyl-4-oxo-1-(phenylcarbonyl)-3-pyrrolidinecarboxylate (2.746 g, 86% yield) as a colorless oil. LCMS: (M+H)+: 276.1.

Workup

  1. stirringthe mixture was stirred for an additional 2 h at 60° C
  2. concentrationThe mixture was then concentrated in vacuo
  3. customthe residue was partitioned between DCM (200 mL) and 1 N aq. HCl (100 mL)
  4. dry with materialThe organic phase was dried over anhydrous MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ab1f799e40c34a60a5dfe270c6d6a44f
Source dataset
uspto-grants-2011_02
Patent number
US07893056B2

Reaction notes

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