Methyl iodide → 1-Benzyl 2-methyl 4-methoxypyrrolidine-1,2-dicarboxylate

HRID 81134Notes

Reaction equation

HRID 81134 reaction equation
[OH:1][C@H:2]1[CH2:6][N:5]([C:7]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:8])[C@H:4]([C:17]([O:19][CH3:20])=[O:18])[CH2:3]1.[CH3:21]I.[H-].[Na+]>C1COCC1>[CH3:21][O:1][CH:2]1[CH2:6][N:5]([C:7]([O:9][CH2:10][C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)=[O:8])[CH:4]([C:17]([O:19][CH3:20])=[O:18])[CH2:3]1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 6884112-Methyl 1-(phenylmethyl) (2S,4R)-4-hydroxy-1,2-pyrrolidinedicarboxylate

Product 1

HCID 140361701-Benzyl 2-methyl 4-methoxypyrrolidine-1,2-dicarboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 1-benzyl 2-methyl (2S,4R)-4-hydroxypyrrolidine-1,2-dicarboxylate (500 mg, 1.79 mmol) in THF (6 mL) was added methyl iodide (0.385 mL) followed by sodium hydride (95 mg, 3.94 mmol). The reaction was stirred for 1 hour, then quenched with ice and diluted with diethyl ether. The organic layer was washed with water and brine, dried over sodium sulfate, filtered, and concentrated under reduced pressure to afford 1-benzyl 2-methyl 4-methoxypyrrolidine-1,2-dicarboxylate. MS ESI calc'd. for C15H19NO5 [M+H]+ 294. found 294.

Workup

  1. customquenched with ice
  2. additiondiluted with diethyl ether
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-92931163832a44aaaf45107d1f5e9d02
Source dataset
uspto-grants-2014_09
Patent number
US08846657B2

Reaction notes

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