Cesium carbonate → 1-[3-Chloro-5-(trifluoromethyl)phenyl]pyrrolidin-3-ol

HRID 2198053ノート

反応式

HRID 2198053 の反応式
Br[C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[C:4]([Cl:12])[CH:3]=1.[OH:13][CH:14]1[CH2:18][CH2:17][NH:16][CH2:15]1.C1(P(C2C=CC=CC=2)C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+]>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O>[Cl:12][C:4]1[CH:3]=[C:2]([N:16]2[CH2:17][CH2:18][CH:14]([OH:13])[CH2:15]2)[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=1

参加物

8

反応物 4

HCID 10796Cesium carbonateHCID 982104-HydroxypyrrolidineHCID 634876Binap, (A+-)-HCID 202698551-Bromo-3-chloro-5-(trifluoromethyl)benzene

生成物 1

HCID 670222091-[3-Chloro-5-(trifluoromethyl)phenyl]pyrrolidin-3-ol収率 80.3%

試薬・触媒・溶媒 3

HCID 167845palladium(II) acetate触媒HCID 962Water溶媒HCID 1140Toluene溶媒

実験手順

A solution of 1-bromo-3-chloro-5-(trifluoromethyl)benzene (5.0 g), 3-hydroxypyrrolidine (1.85 g), palladium(II) acetate (217 mg), (±)-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (1.2 g) and cesium carbonate (18.8 g) in toluene (96 mL) was stirred under an argon gas atmosphere at 85° C. for 16 hr. After cooling to room temperature, water was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated, and the residue was purified by silica gel column chromatography (hexane/ethyl acetate 80:20-10:90) to give the title compound (4.11 g, yield 80%) as a brown oil.

後処理

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated
  6. customthe residue was purified by silica gel column chromatography (hexane/ethyl acetate 80:20-10:90)

出典と根拠

ORDレコード
ord-b36106639f6a4de0b414f5e6b2335ad4
出典データセット
uspto-grants-2012_12
特許番号
US08338622B2

反応ノート

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