Peracetic Acid → 6-(Cyclopropyloxy)-3-pyridinol

HRID 533903Notes

Reaction equation

HRID 533903 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([O:8][CH:9]2[CH2:11][CH2:10]2)=[N:6][CH:7]=1.[Li]CCCC.C[O:18]B(OC)OC.C(OO)(=O)C.OS([O-])=O.[Na+]>C1COCC1>[CH:9]1([O:8][C:5]2[N:6]=[CH:7][C:2]([OH:18])=[CH:3][CH:4]=2)[CH2:11][CH2:10]1

Participants

7

Reactant 5

HCID 6585Peracetic AcidHCID 8470Trimethyl borateHCID 23665763Sodium BisulfiteHCID 722210635-Bromo-2-cyclopropoxypyridineHCID 178418339Butyllithium

Product 1

HCID 867150946-(Cyclopropyloxy)-3-pyridinol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 5-bromo-2-cyclopropoxypyridine (Milestone Pharmtech, 500 mg) in THF (10 mL) was cooled (−78° C.) and n-BuLi (2.5 M in toluene, 1.49 mL) was added dropwise within 10 minutes. After 20 minutes trimethylborate (429 μL) was added. After 2 hours peracetic acid (32% in AcOH, 786 μL) was added dropwise. After 10 minutes the reaction temperature was changed to 0° C. After 1 hour the mixture was poured into aqueous NaHSO3-solution (5%, 5 mL). The mixture was extracted with EA. The organic phase was dried (Na2SO4), filtered and concentrated. The residue was purified by chromatography (silica gel, heptane to EA/heptane 2:3) to provide the subtitle compound. MS ESI+: m/z=152 [M+H]+.

Workup

  1. additionwas added dropwise within 10 minutes
  2. extractionThe mixture was extracted with EA
  3. dry with materialThe organic phase was dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by chromatography (silica gel, heptane to EA/heptane 2:3)

Sources & evidence

ORD record
ord-4773ed77029c44e1bbc739182f622ed5
Source dataset
uspto-grants-2014_10
Patent number
US08853412B2

Reaction notes

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