9-Borabicyclo(3.3.1)nonane → 5-Hydroxy-3-(2-methyl-pyrimidin-5-yl)-pentanoic acid ethyl ester

HRID 2187371Notes

Reaction equation

HRID 2187371 reaction equation
[CH2:1]([O:3][C:4](=[O:16])[CH2:5][CH:6]([C:9]1[CH:10]=[N:11][C:12]([CH3:15])=[N:13][CH:14]=1)[CH:7]=[CH2:8])[CH3:2].B1C2CCCC1CCC2.C([O-])(O)=[O:27].[Na+]>O>[CH2:1]([O:3][C:4](=[O:16])[CH2:5][CH:6]([C:9]1[CH:10]=[N:11][C:12]([CH3:15])=[N:13][CH:14]=1)[CH2:7][CH2:8][OH:27])[CH3:2]

Participants

5

Reactant 3

HCID 789669-Borabicyclo(3.3.1)nonaneHCID 516892Sodium BicarbonateHCID 235812733-(2-Methyl-pyrimidin-5-yl)-pent-4-enoic acid ethyl ester

Product 1

HCID 235812815-Hydroxy-3-(2-methyl-pyrimidin-5-yl)-pentanoic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred solution of 2-4 (422 mg, 1.92 mmol) in TBF was added 5.75 mL of 9-BBN (0.5 M/THF). After 18 hours, a slurry of NaBO3 (2.35 g) and NaHCO3 (2.42 g) in H2O (10 mL) was added and the mixture stirred vigorously for 1 hour. The mixture was extracted with CHCl3, washed with brine, and dried over MgSO4. Following evaporative removal of the solvent, the residue was chromatographed (silica gel, 3% EtOH/EtOAc) to give 2-5 as a clear oil.

Workup

  1. extractionThe mixture was extracted with CHCl3
  2. washwashed with brine
  3. dry with materialdried over MgSO4
  4. customremoval of the solvent
  5. customthe residue was chromatographed (silica gel, 3% EtOH/EtOAc)

Sources & evidence

ORD record
ord-e7e0fb571f0f429b886488fbbd45b041
Source dataset
uspto-grants-2002_06
Patent number
US06410526B1

Reaction notes

Loading…