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

HRID 595930Notes

Reaction equation

HRID 595930 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([CH2:14]I)[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)=[CH:4][N:3]=1.CCC(C)[BH-](C(C)CC)C(C)CC.[Na+].O>C1COCC1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([CH3:14])[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 5129077N-Selectride®HCID 1180452242-fluoro-5-(4-(iodomethyl)tetrahydro-2H-pyran-4-yl)pyridine

Product 1

HCID 1180455832-fluoro-5-(4-methyltetrahydro-2H-pyran-4-yl)pyridineYield 54.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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.

Workup

  1. customThe solution was recooled in an ice bath
  2. stirringThe resulting solution was stirred for 10 min
  3. customThe solvent was removed under vacuum
  4. dissolutionthe residue was dissolved in DCM
  5. filtrationInsoluble solid was filtered
  6. customthe filtrate was purified by flash column chromatography on silica gel (ISCO)
  7. washeluting with 0-80% ethyl acetate in heptane

Sources & evidence

ORD record
ord-e6e2e934e7b54a5288890d53e81fb758
Source dataset
uspto-grants-2016_01
Patent number
US09242996B2

Reaction notes

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