Boron tribromide → (2R*,4S*)-4-(3-fluoro-2-methoxyphenyl)-2-hydroxy-2-(trifluoromethyl)pentanal

HRID 1362468ノート

反応式

HRID 1362468 の反応式
[F:1][C:2]1[C:3]([O:30][CH3:31])=[C:4]([C@H:8]([CH3:29])[CH2:9][C@@:10]([C:25]([F:28])([F:27])[F:26])([OH:24])[CH:11]=NC2C=CC=C3C=2C=CC(C)=N3)[CH:5]=[CH:6][CH:7]=1.B(Br)(Br)Br.C([O-])(O)=[O:37].[Na+]>C(Cl)Cl>[F:1][C:2]1[C:3]([O:30][CH3:31])=[C:4]([C@@H:8]([CH3:29])[CH2:9][C@:10]([OH:24])([C:25]([F:26])([F:27])[F:28])[CH:11]=[O:37])[CH:5]=[CH:6][CH:7]=1

参加物

5

反応物 3

HCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 25180226(2R*,4R*)-4-(3-fluoro-2-methoxyphenyl)-1-[(2-methylquinolin-5-yl)imino]-2-(trifluoromethyl)pentan-2-ol

生成物 1

HCID 86615316(2R*,4S*)-4-(3-fluoro-2-methoxyphenyl)-2-hydroxy-2-(trifluoromethyl)pentanal

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

175 mg (0.60 mmol) of (2R*,4R*-4-(3-fluoro-2-methoxyphenyl)-2-hydroxy-2-(trifluoromethyl)pentanal, 103 mg (0.63 mmol) of 5-amino-2-methylquinoline and 0.3 ml of titanium tetraethoxide are stirred in 20 ml of toluene at 100° C. for 2 h. After the mixture is cooled, it is poured into water, with vigorous stirring to follow. The suspension is filtered through Celite, the filter bed being rinsed thoroughly with ethyl acetate. The phases of the filtrate are separated and extraction is carried out again using ethyl acetate. The extracts are dried over sodium sulphate and the solvent is removed in vacuo to give 230 mg of (2R*,4R*)-4-(3-fluoro-2-methoxyphenyl)-1-[(2-methylquinolin-5-yl)imino]-2-(trifluoromethyl)pentan-2-ol as a crude product. 230 mg of the crude imine in 12 ml of CH2Cl2 are admixed dropwise at −30° C. with 6 ml (6 mmol) of a 1 M boron tribromide solution. The batch is allowed to warm to room temperature and is stirred for 2 hours. It is admixed with saturated NaHCO3 solution, the phases are separated, the aqueous phase is extracted with CH2Cl2 and the combined organic phases are dried (Na2SO4) and concentrated in vacuo. Column chromatography on silica gel (hexane/ethyl acetate 0-75%) yields 145 mg of product.

後処理

  1. customthe phases are separated
  2. extractionthe aqueous phase is extracted with CH2Cl2
  3. dry with materialthe combined organic phases are dried (Na2SO4)
  4. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-80fcc0f630c646bd8b0c53181e72abab
出典データセット
uspto-grants-2011_02
特許番号
US07880042B2

反応ノート

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