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

HRID 595930노트

반응식

HRID 595930 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-e6e2e934e7b54a5288890d53e81fb758
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09242996B2

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