Trifluoroacetic acid → methyl 9-bromo-2,3,4,5-tetrahydro-1H-1-benzoazonin-6-carboxylate

HRID 1810790노트

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HRID 1810790 반응식
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:13](CC3C=CC(OC)=CC=3)[CH2:12][CH2:11][CH2:10][CH2:9][C:8]([C:23]([O:25][CH3:26])=[O:24])=[CH:7][C:6]=2[CH:27]=1.FC(F)(F)C(O)=O>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[NH:13][CH2:12][CH2:11][CH2:10][CH2:9][C:8]([C:23]([O:25][CH3:26])=[O:24])=[CH:7][C:6]=2[CH:27]=1

참가 물질

4

반응물 2

HCID 6422Trifluoroacetic acidHCID 68650162methyl 9-bromo-1-(4-methoxybenzyl)-2,3,4,5-tetrahydro-1H-1-benzoazonin-6-carboxylate

생성물 1

HCID 68649852methyl 9-bromo-2,3,4,5-tetrahydro-1H-1-benzoazonin-6-carboxylate수율 82.1%

시약·촉매·용매 1

HCID 1140Toluene용매

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온도
80 °C

실험 절차

To a solution of methyl 9-bromo-1-(4-methoxybenzyl)-2,3,4,5-tetrahydro-1H-1-benzoazonin-6-carboxylate (12.5 g) in toluene (62.5 ml) was added trifluoroacetic acid (62.5 ml) and the mixture was stirred under nitrogen atmosphere at 80° C. for 7 hours. After distilling off the solvent under reduced pressure, water was added at 0° C. and the mixture was neutralized with potassium carbonate, and extracted with ethyl acetate. After washing the organic layer with aqueous saturated sodium bicarbonate solution and saturated brine, the resultant was dried with magnesium sulfate. The solvent was distilled off under reduced pressure, and the resulting residue was purified by silica gel column chromatography (hexane-ethyl acetate=9:1) and recrystallized from hexane:ethyl acetate to give methyl 9-bromo-2,3,4,5-tetrahydro-1H-1-benzoazonin-6-carboxylate (7.4 g) as yellow crystals.

후처리

  1. distillationAfter distilling off the solvent under reduced pressure, water
  2. additionwas added at 0° C.
  3. extractionextracted with ethyl acetate
  4. washAfter washing the organic layer with aqueous saturated sodium bicarbonate solution and saturated brine
  5. dry with materialthe resultant was dried with magnesium sulfate
  6. distillationThe solvent was distilled off under reduced pressure
  7. customthe resulting residue was purified by silica gel column chromatography (hexane-ethyl acetate=9:1)
  8. customrecrystallized from hexane

출처 및 근거

ORD 기록
ord-d81eb484a3324e65a13e085ab659d9bf
출처 데이터셋
uspto-grants-2013_01
특허 번호
US08362058B2

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