反応 #683112

反応方程式

water

2-fluoro-5-(4-(iodomethyl)tetrahydro-2H-pyran-4-yl)pyridine

N-selectride

→

2-fluoro-5-(4-methyltetrahydro-2H-pyran-4-yl)pyridine

収率 54.8%

溶媒

THF

反応条件

後処理

1. 1
   その他The solution was recooled in an ice bath
2. 2
   workup.STIRRINGThe resulting solution was stirred for 10 min
3. 3
   その他The solvent was removed under vacuum
4. 4
   workup.DISSOLUTIONthe residue was dissolved in DCM
5. 5
   ろ過Insoluble solid was filtered
6. 6
   その他the filtrate was purified by flash column chromatography on silica gel (ISCO)
7. 7
   洗浄eluting with 0-80% ethyl acetate in heptane

実験手順

To a solution of (2-fluoro-5-(4-(iodomethyl)tetrahydro-2H-pyran-4-yl)pyridine (330 mg, 1.03 mmol) in THF (5 mL) at −15° C., was added N-selectride (2.26 mL, 2.26 mmol) dropwise. The solution was stirred at ambient temperature for 16 h. The solution was recooled in an ice bath, and 0.3 mL of water was added. The resulting solution was stirred for 10 min. The solvent was removed under vacuum, and the residue was dissolved in DCM. Insoluble solid was filtered, and the filtrate was purified by flash column chromatography on silica gel (ISCO) eluting with 0-80% ethyl acetate in heptane to give to 2-fluoro-5-(4-methyltetrahydro-2H-pyran-4-yl)pyridine (110 mg, 0.56 mmol, 54.8% yield) as colorless oil with >90% purity. LCMS (m/z): 196 (MH+), 0.64 min.

出典