反应详情

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).

1. temperaturethe reaction was warmed to 0 OC for 45 min
2. customThe reaction was quenched with H20
3. custompartitioned between 100 mL H20 and 100 mL CH2C-2
4. customAfter separating phases
5. extractionthe aqueous layer was extracted with 100 mL CH2C-2
6. washThe combined organic layers were washed with 100 mL brine
7. dry with materialdried over Na2SO4
8. concentrationconcentrated under vacuum
9. customThe residue was purified by flash chromatography
10. washeluting with 2% MeOH in CH2C12