反应详情

To a solution of (3R)-1-(tert-butoxycarbonyl)-3-((3-fluorophenoxy)benzoyl)piperidine (0.95 g, 2.37 mmol) in THF (3 mL) at −20° C. was added 1.45 M 4-methoxybutyl magnesium chloride in THF (3.3 mL, 4.76 mmol) dropwise. The resulting solution was warmed to rt slowly, and the completion of reaction was confirmed by LC-MS (˜20 min). The reaction was quenched with sat'd aq NH4Cl (4 mL) and extracted with Et2O (4×5 mL). The combined organic layers were washed with water and brine, and the solvent was removed in vacuo to give a crude product which was purified by flash column chromatography to afford (R)-tert-butyl 3-((S)-1-(2-(3-fluorophenoxy)phenyl)-1-hydroxy-5-methoxypentyl)piperidine-1-carboxylate (0.50 g, 43%).

1. customthe completion of reaction
2. customwas confirmed by LC-MS (˜20 min)
3. customThe reaction was quenched with sat'd aq NH4Cl (4 mL)
4. extractionextracted with Et2O (4×5 mL)
5. washThe combined organic layers were washed with water and brine
6. customthe solvent was removed in vacuo
7. customto give a crude product which
8. customwas purified by flash column chromatography