Ethyl Acetate → HCID 66733609, compound

Participants

Reaction Conditions

Reaction Steps

1,6-bis(tert-butoxycarbonyl)piperidine-3-carboxylic acid (41.4 mmol, 13.6 g) and N,N′-carbonyldiimidazole (CDI) (51.75 mmol, 8.4 g) in anhydrous THF (140 mL) were stirred 16 h at room temperature under argon. In a separate, sealed and argon-flushed flask, lithium HMDS (1.0 M in THF, 86.9 mmol) is added to 80 mL anhydrous THF stirring at −78° C. To this solution is added dropwise anhydrous ethyl acetate (89 mmol, 8.69 mL). This solution is allowed to stir at −78° C. for 1 hour prior to the dropwise addition of the original CDI/acid solution that had been stirred overnight. The reaction mixture is allowed to stir and warm to room temperature overnight. The reaction is then quenched with saturated NH4Cl(aq) (250 mL) and extracted with Et2O (100×2). The combined organics are then washed with water, saturated brine, and dried over Na2SO4. The solvent is removed in vacuo and the residue (12.6 g) was used in the next step without further purification.

Provenance & Evidence