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

HRID 1852745Notes

Reaction equation

HRID 1852745 reaction equation
[OH:1][CH:2]([CH:4]1[CH2:8][CH2:7][CH2:6][N:5]1[C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH3:3].[CH3:16]I.[H-].[Na+]>CN(C=O)C>[CH3:16][O:1][CH:2]([CH:4]1[CH2:8][CH2:7][CH2:6][N:5]1[C:9]([O:11][C:12]([CH3:14])([CH3:13])[CH3:15])=[O:10])[CH3:3]

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

To a mixture of tert-butyl 2-(1-hydroxyethyl)pyrrolidine-1-carboxylate (750 mg, 3.48 mmol) in DMF (12 mL) at 0° C. was added methyl iodide (0.75 mL, 11.98 mmol) followed by sodium hydride (184 mg, 7.66 mmol). The mixture was stirred for 2 hours at room temperature. The reaction was quenched with ice and diluted with diethyl ether. The organic layer was washed with water and brine, dried over sodium sulfate, and filtered and concentrated under reduced pressure to afford tert-butyl 2-(1-methoxyethyl)pyrrolidine-1-carboxylate. 1H NMR (500 MHz, CDCl3) δ 3.92-3.45 (m, 2H), 3.45-3.23 (m, 4H), 2.11-1.66 (m, 4H), 1.63 (s, 1H), 1.46 (s, 9H), 1.04 (dd, J=6.3, 30.8, 3H).

Workup

  1. customThe reaction was quenched 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-d8b1f649e4764002961e1ee91d828858
Source dataset
uspto-grants-2015_02
Patent number
US08962611B2

Reaction notes

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