Formaldehyde → 5-methyl-2,3,3a,4,5,9b-hexahydro-1H-cyclopenta[c]quinoline

HRID 505019

반응식

HRID 505019 반응식
[CH3:1][NH:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH:9]1[CH2:13][CH2:12][CH2:11][CH:10]=1.C=O.B(F)(F)F.[CH3:20]COCC.[OH-].[Na+]>C(#N)C>[CH3:1][N:2]1[C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=2[CH:10]2[CH2:11][CH2:12][CH2:13][CH:9]2[CH2:20]1

참가 물질

7

반응물 5

HCID 712FormaldehydeHCID 7515N-MethylanilineHCID 8000Boron trifluoride etherateHCID 8882CyclopenteneHCID 14798Sodium Hydroxide

생성물 1

HCID 37437055-methyl-2,3,3a,4,5,9b-hexahydro-1H-cyclopenta[c]quinoline수율 57.7%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

반응 조건

온도
1.5 °C

실험 절차

N-methyl aniline (1.07 g, 10.0 mmol) was dissolved in 23 ml acetonitrile under N2 atmosphere. Cyclopentene (4.08 g, 60.0 mmol) and paraformaldehyde (300 mg, 10.0 mmol) were added in one portion. The mixture was cooled to 1.5° C. and BF3.OEt2 (3.55 g, 25.0 mmol) was added over a period of 2 minutes. The cooling bath was removed after addition was completed (reaction temp=9° C.). The reaction was completed after 2 hours (HPLC). NaOH (10.5 g in 20 ml water) was added and the mixture stirred overnight. Layers were separated. An inorganic solid was separated by filtration and the organic layer was extracted with ethyl acetate 3×10 ml. The combined organic layers were washed with brine and dried over MgSO4. Evaporation of solvent and flash-chromatography with heptane/ethyl acetate gave 5-Methyl-2,3,3a,4,5,9b-hexahydro-1H-cyclopenta[c]quinoline (1.08 g, 57% yield).

후처리

  1. customThe cooling bath was removed
  2. additionafter addition
  3. custom(reaction temp=9° C.)
  4. customLayers were separated
  5. customAn inorganic solid was separated by filtration
  6. extractionthe organic layer was extracted with ethyl acetate 3×10 ml
  7. washThe combined organic layers were washed with brine
  8. dry with materialdried over MgSO4
  9. customEvaporation of solvent and flash-chromatography with heptane/ethyl acetate

출처 및 근거

ORD 기록
ord-47ec983ca27e4a8f8febbe18aa5c5fba
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07781427B2

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