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

HRID 81137Notes

Reaction equation

HRID 81137 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-37e27444e3924a9282661b8abf3a8b5f
Source dataset
uspto-grants-2014_09
Patent number
US08846657B2

Reaction notes

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