1-Methoxy-3-trimethylsilyloxy-1,3-butadiene → 3,4,5,6-Tetrahydrobenzo[c]quinolizin-3-(4aH)-one

HRID 380452

반응식

HRID 380452 반응식
C[C:2]1[C:3](=[O:17])[CH2:4][CH2:5][N:6]2[C:11]=1[CH2:10][CH2:9][C:8]1[CH:12]=[C:13](C)[CH:14]=[CH:15][C:7]2=1.COC=CC(O[Si](C)(C)C)=C.C([O-])(O)=O.[Na+]>C(Cl)Cl.Cl[Ti](Cl)(Cl)Cl>[CH:5]1[N:6]2[CH:11]([CH2:2][C:3](=[O:17])[CH:4]=1)[CH2:10][CH2:9][C:8]1[CH:12]=[CH:13][CH:14]=[CH:15][C:7]2=1

참가 물질

6

반응물 3

HCID 1010511-Methoxy-3-trimethylsilyloxy-1,3-butadiene2회HCID 516892Sodium BicarbonateHCID 10220187AS-601811

생성물 1

HCID 104427523,4,5,6-Tetrahydrobenzo[c]quinolizin-3-(4aH)-one수율 25.1%

시약·촉매·용매 2

HCID 24193Titanium Tetrachloride촉매HCID 6344Dichloromethane용매2회

실험 절차

To a stirred solution of compound 4 [(QW)n=H, R3=R4=H] (4 g, 14.42 mmol) of the example 3, in 75 ml of anhydrous CH2Cl2 under argon at −10° C. is added, dropwise in 7 min, 28.84 ml of a 1M solution of TiCl4 in CH2Cl2 maintaining the temperature below −5° C. Then 1-methoxy-3-(trimethylsilyloxy)-1-3-butadiene (compound 6, R1=MeO, R2=H, R6=H) (3.29 ml, 17.3 mmol) is added by syringe at 0° C., and the reaction was left aside at room temperature for 1 h. The reaction mixture is added, cautiously, with 100 ml of NaHCO3 satured solution, and then stirred for 30 min. The organic layer is separated, washed with water, filtered on Celite and dried over Na2SO4. After removal of the solvent the crude product is purified by flash column chromatography (eluant light-petroleum ether/ethyl acetate 1:4) affording 0.72 g (25% yield) of the expected product (white crystals, m.p.: 135-137° C.).

후처리

  1. customthe temperature below −5° C
  2. additionThe reaction mixture is added
  3. customThe organic layer is separated
  4. washwashed with water
  5. filtrationfiltered on Celite
  6. dry with materialdried over Na2SO4
  7. customAfter removal of the solvent the crude product
  8. customis purified by flash column chromatography (eluant light-petroleum ether/ethyl acetate 1:4)

출처 및 근거

ORD 기록
ord-33c1855d72ca466e9a3ad6b1d107fe27
출처 데이터셋
uspto-grants-2001_10
특허 번호
US06303622B1

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