反应详情

[4-((S)-3-Oxo-cyclopentyl)-phenyl]-carbamic acid benzyl ester (618 mg, 2 mmol, 1 equiv.) was dissolved in DCE (20 mL). To this solution was transferred a solution of 2-methylpyrrolidine (212 mg, 2.5 mmol, 1.25 equiv.) in 3 mL of DCE, followed by acetic acid (360 mg, 6 mmol, 3 equiv) in DCE (2 mL), then by addition of powder NaBH(OAc)3 (1.27 g, 6 mmol, 3 equiv.) in one portion under N2 at r.t. The yellowish milky solution was stirred at r.t. 24 h. The reaction was diluted with DCM (20 mL) and quenched with 10 mL of NaHCO3. The two layers were separated, and the aqueous layer was extracted with DCM (10 mL×2). The combined DCM extracts were washed with sodium bicarbonate (10 mL), brine (15 mL), dried (anhydrous potassium carbonate), filtered, and concentrated. The residue, a thick oil, was dissolved in DCM, and purified on a silica gel column to afford 0.61 g (81%) of the title compound.

1. custom24 h
2. customquenched with 10 mL of NaHCO3
3. customThe two layers were separated
4. extractionthe aqueous layer was extracted with DCM (10 mL×2)
5. washThe combined DCM extracts were washed with sodium bicarbonate (10 mL), brine (15 mL)
6. dry with materialdried (anhydrous potassium carbonate)
7. filtrationfiltered
8. concentrationconcentrated
9. dissolutionThe residue, a thick oil, was dissolved in DCM
10. custompurified on a silica gel column