Hydrochloric Acid → (1S,2R)-4-(2-hydroxy-1-methyl-4-pyridin-3-ylbutoxy)benzeneboronic acid

HRID 379997

Reaction equation

HRID 379997 reaction equation
[Si]([O:8][C@H:9]([CH2:22][CH2:23][C:24]1[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=1)[C@H:10]([CH3:21])[O:11][C:12]1[CH:17]=[CH:16][C:15]([B:18]([OH:20])[OH:19])=[CH:14][CH:13]=1)(C(C)(C)C)(C)C.Cl>CO>[OH:8][C@H:9]([CH2:22][CH2:23][C:24]1[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=1)[C@H:10]([CH3:21])[O:11][C:12]1[CH:13]=[CH:14][C:15]([B:18]([OH:20])[OH:19])=[CH:16][CH:17]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 54020751(1S,2R)-4-[2-(tert-butyldimethylsilanyloxy)-1-methyl-4-pyridin-3-ylbutoxy]benzeneboronic acid

Product 1

HCID 54413593(1S,2R)-4-(2-hydroxy-1-methyl-4-pyridin-3-ylbutoxy)benzeneboronic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of (1S,2R)-4-[2-(tert-butyldimethylsilanyloxy)-1-methyl-4-pyridin-3-ylbutoxy]benzeneboronic acid (10 g, Example 11) in methanol (150 ml) was stirred for 16 hours at room temperature and 2M hydrochloric acid (25 ml). The solution was concentrated to give an acidic aqueous residue which was washed with diethyl ether. The aqueous layer was basified with saturated sodium bicarbonate, the product was extracted into ethyl acetate, dried over anhydrous magnesium sulfate, filtered and concentrated to give the title compound as a foam. (6.97 g).

Workup

  1. concentrationThe solution was concentrated
  2. customto give an acidic aqueous residue which
  3. washwas washed with diethyl ether
  4. extractionthe product was extracted into ethyl acetate
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-0b5ae360856b4c229a79a8f685df2c77
Source dataset
uspto-grants-2001_10
Patent number
US06300352B1

Linked notes

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