Pyridine → HCID 67256139, compound

Participants

Reaction Steps

A solution of 3-methoxy -4-nitro-benzoyl chloride (608 mg, 2.82 mmol) in 10 mL of CH2Cl2 was added to stirred solution of 500 mg (2.82 mmol) of (3S)-1-benzyl-pyrrolidin-3-ol and 1 mL of pyridine in 15 mL CH2Cl2 at room temperature. After stirring for 18 h, the reaction mixture was diluted with 20 mL of saturated aqueous NaHCO3, and extracted with CH2Cl2 (2×10 mL). The combined extracts were washed with 20 mL of brine, dried over MgSO4, filtered, and concentrated in vacuo to furnish 780 mg (71%) of the desired ester as a yellow oil, which solidified after drying under high vacuum. The resulting solid was further purified by trituration with 1:1 ether-hexane. 1H-NMR (400 MHz, CDCl3) δ7.83 (d, J =7.83 Hz, 1H), 7.74 (s, 1H), 7.68 (d, J=7.83 Hz, 1H), 7.2-7.4 (m, 5H), 5.44 (br.m, 1H), 4.02 (s, 2H), 3.69 (dd, J=30 Hz, J=13 Hz, 1H), 2.8-3.0 (m, 2H), 2.5-2.6 (m, 1H), 2.3-2.45 (m, 1H), 2.0-2.1 (m, 1H)

Provenance & Evidence