Acetyl chloride → HCID 10590693, compound

Participants

Reaction Steps

Acetyl chloride (1.50 ml, 21.10 mmol) was added dropwise to MeOH (7.5 mL) at 0° C. After 15 min of stirring a solution of 3-((2R,5S)-1-benzyl-5-(tert-butoxycarbonyl)pyrrolidin-2-yl)propanoic acid (200 mg, 0.600 mmol) in MeOH (7.5 mL) was slowly added to the reaction. The reaction mixture was then heated at reflux overnight. The reaction was concentrated. The residue was partitioned between EtOAc and 10% Na2CO3. The organic phase was separated, washed with saturated aqueous NaCl solution, dried over MgSO4, filtered and concentrated. The resulting residue was purified using silica gel chromatography (ISCO system) to give the product (2S,5R)-methyl 1-benzyl-5-(3-methoxy-3-oxopropyl)pyrrolidine-2-carboxylate (126 mg, 0.413 mmol, 68.8% yield) as colorless syrup. 1HNMR (400 MHz, CDCl3) δ ppm 7.35-7.17 (5 H, m), 3.95 (1 H, d, J=13.7 Hz), 3.71-3.61 (4 H, m), 3.47 (3 H, s), 3.37-3.26 (1 H, m), 2.86-2.73 (1 H, m), 2.53-2.41 (1 H, m), 2.38-2.25 (1 H, m), 2.08-1.79 (4 H, m), 1.79-1.66 (1 H, m), 1.66-1.53 (1 H, m).

Provenance & Evidence