Tetrahydrofuran → HCID 86620019, 화합물

HRID 909370노트

반응식

HRID 909370 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH2:12][CH2:11][CH2:10][CH:9]=2)=[CH:4][N:3]=1.C1C[O:16]CC1>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:12][CH2:11][CH2:10][CH2:9]2)=[CH:4][N:3]=1.[Cl:1][C:2]1[N:3]=[CH:4][C:5]([C:8]2([OH:16])[CH2:12][CH2:11][CH2:10][CH2:9]2)=[CH:6][CH:7]=1

참가 물질

4

반응물 2

HCID 8028TetrahydrofuranHCID 59265941HCID 59265941, 화합물

생성물 2

HCID 592659571-(6-Chloro-pyridin-3-yl)cyclopentanol수율 26%HCID 86620019HCID 86620019, 화합물수율 29%

실험 절차

2-Chloro-5-(cyclopent-1-enyl)pyridine (1.5 g, 8.5 mmol) was dissolved in THF (30 mL) in an oven-dried, nitrogen-flushed 250 mL round bottom flask and the resulting solution cooled in a dry ice/acetone bath under nitrogen. BH3.THF complex (2.4 g, 28.0 mmol, 28 mL of a 1 M solution in THF) was added dropwise with stirring via syringe and the mixture was allowed to warm slowly to room temperature and stir overnight. 2 N NaOH (15 mL), ethanol (15 mL) and 35% H2O2 (10 mL) were added and the mixture stirred for 0.5 h then diluted with EtOAc and 1 N HCl. The layers were separated and the organic layer washed with brine and aq. NaHSO3, dried over Na2SO4, filtered through celite and concentrated. Purification by flash chromatography (hexanes:EtOAc/10:1→2:1) gave in order of elution by-products 2-chloro-5-cyclopentylpyridine (0.45 g, 29%) and 1-(6-chloropyridin-3-yl)-cyclopentanol (0.44 g, 26%) followed by the desired product trans-2-(6-chloropyridin-3-yl)cyclopentanol (0.25 g, 15%) as a clear oil: LC/MS (ESI) m/z 197, 1H NMR (300 MHz, CDCl3) δ 8.26 (d, 1H, J=2.4 Hz), 7.55 (dd, 1H, J=8.4, 2.4 Hz), 7.25 (d, 1H, J=8.4 Hz), 4.12 (m, 1H), 2.88 (m, 1H), 2.24-1.62 (m, 6H).

후처리

  1. customflushed 250 mL round bottom flask
  2. temperaturethe resulting solution cooled in a dry ice/acetone bath under nitrogen
  3. additionBH3.THF complex (2.4 g, 28.0 mmol, 28 mL of a 1 M solution in THF) was added dropwise
  4. stirringstir overnight
  5. addition2 N NaOH (15 mL), ethanol (15 mL) and 35% H2O2 (10 mL) were added
  6. stirringthe mixture stirred for 0.5 h
  7. additionthen diluted with EtOAc and 1 N HCl
  8. customThe layers were separated
  9. washthe organic layer washed with brine and aq. NaHSO3
  10. dry with materialdried over Na2SO4
  11. filtrationfiltered through celite and
  12. concentrationconcentrated
  13. customPurification by flash chromatography (hexanes:EtOAc/10:1→2:1)

출처 및 근거

ORD 기록
ord-c54d0418eea7413f84b9f51ee2a395b1
출처 데이터셋
uspto-grants-2011_09
특허 번호
US08017788B2

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