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

HRID 1386019Notes

Reaction equation

HRID 1386019 reaction equation
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

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-7ccfb72c2a044278abab7e0f2867a059
Source dataset
uspto-grants-2001_07
Patent number
US06265409B1

Reaction notes

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