Dimethyl Sulfoxide → 1-Benzyl-3-(SR)-(4-oxopiperidin-1-ylmethyl)-4-(SR)-phenylpyrrolidine

Participants

Reaction Steps

To a solution of 0.14 mL of oxalylchloride in 3 mL of CH2CI2 at -70° C. was added 0.16 mL of DMSO. After 5 min 270 mg of 1-Benzyl-3-(SR)-(4-hydroxypiperidin- 1-ylmethyl)-4-(SR)-phenylpyrrolidine (from Example 14) in 3 mL of CH2Cl2 was added. After stirring for 10 min, the reaction was warmed to 0 OC for 45 min. The reaction was quenched with H20 and partitioned between 100 mL H20 and 100 mL CH2C-2. After separating phases, the aqueous layer was extracted with 100 mL CH2C-2. The combined organic layers were washed with 100 mL brine, dried over Na2SO4 and concentrated under vacuum. The residue was purified by flash chromatography eluting with 2% MeOH in CH2C12 to provide 256 mg of the title compound as a light yellow oil. RF : 0.40 (5% MeOH in CH2Cl2). 1H NMR (300 MHz, CDCl3): δ2.2-2.4 (m, 4H), 2.4-2.7 (m, 9H), 2.9-3.1 (m, 3H), 3.7 (ABq, 2H), 7.1-7.4 (m, 10H). Mass Spectrum (ESI): 349.3 (M+H).

Provenance & Evidence