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

HRID 1662527
ノート
印刷プレビュー

反応式

HRID 1662527 の反応式
[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
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028
Tetrahydrofuran
溶媒
2 回

反応条件

温度
0 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-3813813f4fda43c1a291af52a6621885
出典データセット
uspto-grants-2011_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08030354B2

反応ノート

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