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

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

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.