Water → (2R)-4-[2-(tert-butyldimethylsilanyloxy)-4-pyridin-3-yl-butoxy]benzeneboronic acid

HRID 1386019ノート

反応式

HRID 1386019 の反応式
C([Li])CCC.Br[C:7]1[CH:31]=[CH:30][C:10]([O:11][CH2:12][C@H:13]([O:22][Si:23]([C:26]([CH3:29])([CH3:28])[CH3:27])([CH3:25])[CH3:24])[CH2:14][CH2:15][C:16]2[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=2)=[CH:9][CH:8]=1.[B:32](OC(C)C)([O:37]C(C)C)[O:33]C(C)C.O>O1CCCC1.C(OCC)(=O)C>[N:18]1[CH:19]=[CH:20][CH:21]=[C:16]([CH2:15][CH2:14][C@@H:13]([O:22][Si:23]([C:26]([CH3:29])([CH3:28])[CH3:27])([CH3:25])[CH3:24])[CH2:12][O:11][C:10]2[CH:30]=[CH:31][C:7]([B:32]([OH:37])[OH:33])=[CH:8][CH:9]=2)[CH:17]=1

参加物

7

反応物 4

HCID 962WaterHCID 21531Triisopropyl borateHCID 54062431(2r)-1-(4-Bromophenoxy)-4-(3-pyridyl)-2-(tert-butyldimethylsilyloxy)butaneHCID 178418339Butyllithium

生成物 1

HCID 11200434(2R)-4-[2-(tert-butyldimethylsilanyloxy)-4-pyridin-3-yl-butoxy]benzeneboronic acid

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

A solution of n-butyllithium (2.5 M in hexanes, 6.9 ml, CAUTION) was added dropwise to a stirring solution of (2R)-1-(4-bromophenoxy)-4-(3-pyridyl)-2-(tert-butyldimethylsilyloxy)butane (1.50 g, Example 21b)) and triisopropyl borate (4.3 ml) in tetrahydrofuran (200 ml) at −70° C. After the addition was complete the reaction mixture was allowed to warm to room temperature. After 1 hour water (200 ml) and ethyl acetate (200 ml) were added. The organic phase was separated, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to give an oil. This was partly purified by column chromatography over silica eluting with dichloromethane then ethyl acetate then methanol to give the sub-title compound as a glass (2 g).

後処理

  1. additionAfter the addition
  2. customThe organic phase was separated
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customto give an oil
  7. customThis was partly purified by column chromatography over silica eluting with dichloromethane

出典と根拠

ORDレコード
ord-7ccfb72c2a044278abab7e0f2867a059
出典データセット
uspto-grants-2001_07
特許番号
US06265409B1

反応ノート

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