反应详情

A solution of 0.27 mL (2.0 mmol) of (Diethylamino)sulfur trifluoride (DAST) in 2 mL of CH2Cl2 was cooled to −78° C. To this was added a solution of 1-benzyl-4-(3-Phenyl-2-hydroxypropyl)piperidine (Example 228, Step 2) in 2 mL of CH2Cl2. The mixture was stirred and warmed to rt. After 20 min, 10 mL of H2O were added and the mixture was extracted with CH2Cl2. The combined organic fractions were washed with sat'd NaHCO3 solution and sat'd NaCl solution, dried over MgSO4, filtered and the filtrate was concentrated. The residue was purified by chromatography (silica, hexanes:ethyl acetate, 1:1) to give 1-benzyl-4-(3-phenyl-2-fluoropropyl)piperidine. Removal of the benzyl protecting group was achieved under standard conditions.

1. extractionthe mixture was extracted with CH2Cl2
2. washThe combined organic fractions were washed with sat'd NaHCO3 solution
3. dry with materialdried over MgSO4
4. filtrationfiltered
5. concentrationthe filtrate was concentrated
6. customThe residue was purified by chromatography (silica, hexanes:ethyl acetate, 1:1)