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

HRID 453731

반응식

HRID 453731 반응식
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

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 887Methanol용매HCID 7237O-Xylene용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-a16c1904317d4c49a94d0644804d1d59
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08492549B2

연결된 노트

불러오는 중…