Water → 1-[3,5-Bis(trifluoromethyl)phenyl]pyrrolidin-3-ol

HRID 2198020

反応式

HRID 2198020 の反応式
[F:1][C:2]([F:15])([F:14])[C:3]1[CH:4]=[C:5](Br)[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.[OH:16][CH:17]1[CH2:21][CH2:20][NH:19][CH2:18]1.CC(C)([O-])C.[Na+].O>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].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>[F:1][C:2]([F:15])([F:14])[C:3]1[CH:4]=[C:5]([N:19]2[CH2:20][CH2:21][CH:17]([OH:16])[CH2:18]2)[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1

参加物

8

反応物 4

HCID 962WaterHCID 676021-Bromo-3,5-bis(trifluoromethyl)benzeneHCID 982104-HydroxypyrrolidineHCID 23676156Sodium t-butoxide

生成物 1

HCID 752451961-[3,5-Bis(trifluoromethyl)phenyl]pyrrolidin-3-ol収率 61.3%

試薬・触媒・溶媒 3

HCID 634876Binap, (A+-)-触媒HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 1140Toluene溶媒

実験手順

A solution of 3,5-bis(trifluoromethyl)phenyl bromide (21.1 g), 3-hydroxypyrrolidine (6.53 g), tris(dibenzylideneacetone)dipalladium(0) (1.47 g), (±)-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (1.99 g) and sodium tert-butoxide (10.6 g) in toluene (140 ml) was stirred under an argon gas atmosphere at 100° C. for 18 hr. After cooling to room temperature, water was added to the reaction mixture, 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 95:5-70:30) to give the title compound (13.2 g, yield 61%) as colorless crystals.

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 95:5-70:30)

出典と根拠

ORDレコード
ord-6a27d07c863945b19b2ec73161da218e
出典データセット
uspto-grants-2012_12
特許番号
US08338622B2

関連ノート

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