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

HRID 533903ノート

反応式

HRID 533903 の反応式
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

参加物

7

反応物 5

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

生成物 1

HCID 867150946-(Cyclopropyloxy)-3-pyridinol

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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]+.

後処理

  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)

出典と根拠

ORDレコード
ord-4773ed77029c44e1bbc739182f622ed5
出典データセット
uspto-grants-2014_10
特許番号
US08853412B2

反応ノート

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