Methyl iodide → Tert-butyl 2-(1-methoxyethyl)pyrrolidine-1-carboxylate

HRID 2236500Notes

Reaction equation

HRID 2236500 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][CH:9]1[CH:13]([OH:15])[CH3:14])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:16]I.[H-].[Na+]>CN(C)C=O>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][CH:9]1[CH:13]([O:15][CH3:16])[CH3:14])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 23401992Tert-butyl 2-(1-hydroxyethyl)pyrrolidine-1-carboxylate

Product 1

HCID 68691414Tert-butyl 2-(1-methoxyethyl)pyrrolidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-(1-Hydroxy-ethyl)-pyrrolidine-1-carboxylic acid tert-butyl ester (1.0 g, 4.3 mmol) in N,N-dimethylformamide (15 mL) is cooled to 0° C., MeI (1 mL) is added followed by NaH (380 mg, 60% suspension in mineral oil, 9.5 mmol). The resulting mixture is allowed to stir at room temperature for 2 hours until TLC reported no remaining starting material. The reaction is quenched with ice and ether is added. N,N-dimethylformamide is washed away with H2O and the ether layer is dried and concentrated to afford the crude product used directly in the next step.

Workup

  1. customThe reaction is quenched with ice and ether
  2. additionis added
  3. washN,N-dimethylformamide is washed away with H2O
  4. dry with materialthe ether layer is dried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-4f9bb816bc8b4fa5a6c19e47cf15c4aa
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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