3-Phenylpyridine → 1-(2,3-Dihydrobenzo[1,4]dioxin-2-ylmethyl)-5-phenyl-1,2,3,6-tetrahydropyridine

HRID 453731

反応式

HRID 453731 の反応式
Br[CH2:2][CH:3]1[O:8][C:7]2[CH:9]=[CH:10][CH:11]=[CH:12][C:6]=2[O:5][CH2:4]1.[C:13]1([C:19]2[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[BH4-].[Na+]>C1(C)C(C)=CC=CC=1.CO>[O:8]1[C:7]2[CH:9]=[CH:10][CH:11]=[CH:12][C:6]=2[O:5][CH2:4][CH:3]1[CH2:2][N:21]1[CH2:20][C:19]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:24][CH2:23][CH2:22]1

参加物

6

反応物 3

HCID 138863-PhenylpyridineHCID 983332-Bromomethyl-1,4-benzodioxaneHCID 4311764Sodium borohydride

生成物 1

HCID 251745131-(2,3-Dihydrobenzo[1,4]dioxin-2-ylmethyl)-5-phenyl-1,2,3,6-tetrahydropyridine

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 7237O-Xylene溶媒

実験手順

A mixture of 2-bromomethyl-2,3-dihydrobenzo[1,4]dioxine (500 mg, 2.18 mmol) and 3-phenyl-pyridine (339 mg, 2.18 mmol) in xylene (2 ml) was refluxed for 4 h. After cooling, the solvent was decanted to give the crude oily pyridinium salt, which was dissolved in MeOH (5 ml). NaBH4 (330 mg, 4 eq) was added in small portions to the cooled mixture. After stirring for 2 h at RT, MeOH was evaporated, water was added and the mixture extracted with EtOAc. Drying (Na2SO4) and evaporation gave the crude product, which was purified by flash chromatography (heptane/EtOAc).

後処理

  1. temperaturewas refluxed for 4 h
  2. temperatureAfter cooling
  3. customthe solvent was decanted
  4. customto give the crude oily pyridinium salt, which
  5. customMeOH was evaporated
  6. additionwater was added
  7. extractionthe mixture extracted with EtOAc
  8. customDrying
  9. custom(Na2SO4) and evaporation

出典と根拠

ORDレコード
ord-a16c1904317d4c49a94d0644804d1d59
出典データセット
uspto-grants-2013_07
特許番号
US08492549B2

関連ノート

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