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Sodium Hydroxide → (5'-(Difluoromethyl)-2-(2,2-dimethylcyclopentyl)-2'-fluoro-1,1'-biphenyl-4-yl)methanol

HRID 1662527
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HRID 1662527 반응식
[F:1][CH:2]([F:27])[C:3]1[CH:4]=[CH:5][C:6]([F:26])=[C:7]([C:9]2[CH:14]=[CH:13][C:12]([C:15](OC)=[O:16])=[CH:11][C:10]=2[CH:19]2[CH2:23][CH2:22][CH2:21][C:20]2([CH3:25])[CH3:24])[CH:8]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3].[OH-].[Na+]>C1COCC1>[F:27][CH:2]([F:1])[C:3]1[CH:4]=[CH:5][C:6]([F:26])=[C:7]([C:9]2[CH:14]=[CH:13][C:12]([CH2:15][OH:16])=[CH:11][C:10]=2[CH:19]2[CH2:23][CH2:22][CH2:21][C:20]2([CH3:24])[CH3:25])[CH:8]=1
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참가 물질

5

반응물 3

HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 57705984Methyl 5'-(difluoromethyl)-2-(2,2-dimethylcyclopentyl)-2'-fluoro-1,1'-biphenyl-4-carboxylate

생성물 1

HCID 57706837(5'-(Difluoromethyl)-2-(2,2-dimethylcyclopentyl)-2'-fluoro-1,1'-biphenyl-4-yl)methanol수율 77.7%

시약·촉매·용매 1

HCID 8028
Tetrahydrofuran
용매
2회

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온도
0 °C

실험 절차

To a cooled solution of 83.3C (0.86 g, 2.29 mmol) in dry THF (15 mL) at 0° C. was added LAH, 1.0M in THF (4.6 mL, 4.6 mmol) dropwise. Upon complete addition, the reaction was maintained at 0° C. and monitored by TLC and LCMS. After 45 minutes, 1N NaOH was added to quench the reaction (gas evolution occurred). The resulting solution was extracted three times with EtOAc. After drying over anhydrous magnesium sulfate, filtration, and concentration, the residue was purified by flash chromatography (SiO2 gel 60, eluted with 0%-100% EtOAc in hexanes). Fractions containing the desired product were combined and concentrated to provide 83.3D as a colorless oil (0.62 g, 77%). MS ESI (pos.) m/e: 331.0 (M−H2O)+. Chiral separation of 83.3D was accomplished on Chiracel-OD (4% EPA in hexane) to provide 83.3E (peak 1) and 83.3F (peak 2). Both enantiomers were used to synthesize example compounds, and both enantiomers gave active compounds. The enantiomer corresponding to peak 2 provided the more active example compound.

후처리

  1. additionUpon complete addition
  2. customto quench
  3. customthe reaction (gas evolution occurred)
  4. extractionThe resulting solution was extracted three times with EtOAc
  5. dry with materialAfter drying over anhydrous magnesium sulfate, filtration, and concentration
  6. customthe residue was purified by flash chromatography (SiO2 gel 60, eluted with 0%-100% EtOAc in hexanes)
  7. additionFractions containing the desired product
  8. concentrationconcentrated

출처 및 근거

ORD 기록
ord-3813813f4fda43c1a291af52a6621885
출처 데이터셋
uspto-grants-2011_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08030354B2

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