Sodium borohydride → 1-{6-[4-(Trifluoromethyl)phenyl]-2-pyridinyl}-1-pentanol

HRID 1391727노트

반응식

HRID 1391727 반응식
[F:1][C:2]([F:22])([F:21])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:14]=[C:13]([C:15](=[O:20])[CH2:16][CH2:17][CH2:18][CH3:19])[CH:12]=[CH:11][CH:10]=2)=[CH:5][CH:4]=1.[BH4-].[Na+]>C1COCC1.O>[F:21][C:2]([F:1])([F:22])[C:3]1[CH:4]=[CH:5][C:6]([C:9]2[N:14]=[C:13]([CH:15]([OH:20])[CH2:16][CH2:17][CH2:18][CH3:19])[CH:12]=[CH:11][CH:10]=2)=[CH:7][CH:8]=1

참가 물질

5

반응물 2

HCID 4311764Sodium borohydrideHCID 586299011-{6-[4-(Trifluoromethyl)phenyl]-2-pyridinyl}-1-pentanone

생성물 1

HCID 586298221-{6-[4-(Trifluoromethyl)phenyl]-2-pyridinyl}-1-pentanol수율 99.7%

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

A mixture of 1-{6-[4-(trifluoromethyl)phenyl]-2-pyridinyl}-1-pentanone (2.80 g, 9.11 mmol) in THF (61 mL) at 0° C. (ice/water bath) was treated drop-wise with a mixture of sodium borohydride (689 mg, 18.21 mmol) in water (11 mL) over 5-10 minutes. The resulting mixture was stirred at this temperature for 2.5 hours and was then partitioned between EtOAc (200 mL) and water (200 mL) and the layers separated. The aqueous was re-extracted with EtOAc (200 mL) and the combined organic layer washed with brine (250 mL), dried (MgSO4), filtered and reduced. Purification by Biotage™ chromatography (silica) eluting with cyclohexane:EtOAc (gradient 20:1 to 5:1) afforded the title compound as a colourless oil (2.81 g).

후처리

  1. additionwas treated drop-wise
  2. customwas then partitioned between EtOAc (200 mL) and water (200 mL)
  3. customthe layers separated
  4. extractionThe aqueous was re-extracted with EtOAc (200 mL)
  5. washthe combined organic layer washed with brine (250 mL)
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. customPurification by Biotage™ chromatography (silica)
  9. washeluting with cyclohexane

출처 및 근거

ORD 기록
ord-beda19d4626a4e8c874d260255c78966
출처 데이터셋
uspto-grants-2008_03
특허 번호
US07338960B2

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