Methanol → (S)-Methyl 1-methylpyrrolidine-2-carboxylate

Participants

Reaction Steps

To a solution of N-methyl (L)-proline, from step 3a, in methanol at 0° C. is added thionyl chloride (1.1 eq) dropwise, and the reaction mixture is slowly allowed to warm to room temperature. Upon completion of the reaction the solvent is removed in vacuo, and the crude product is dissolved in 10% aq. HCl and washed with ether. The aqueous layer is adjusted to pH ~12 with K2CO3 (solid) and extracted with CH2Cl2. The combined CH2Cl2 layers are dried (MgSO4) and concentrated to afford the crude product as a clear oil.

Provenance & Evidence