N,N,N',N'-Tetramethylethylenediamine → HCID 18630059, 화합물

HRID 368563

반응식

HRID 368563 반응식
[Li]C(CC)C.C1CCCCC1.[CH2:12]([N:14]([CH2:24][CH3:25])[C:15](=[O:23])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[Cl:22])[CH3:13].CN(CCN(C)C)C.[CH3:34][Sn:35](Cl)([CH3:37])[CH3:36]>C1COCC1.CCOCC>[Cl:22][C:17]1[CH:18]=[CH:19][CH:20]=[C:21]([Sn:35]([CH3:37])([CH3:36])[CH3:34])[C:16]=1[C:15]([N:14]([CH2:12][CH3:13])[CH2:24][CH3:25])=[O:23]

참가 물질

8

반응물 5

HCID 8037N,N,N',N'-TetramethylethylenediamineHCID 8078CyclohexaneHCID 14016Trimethyltin chlorideHCID 825662-Chloro-N,N-diethylbenzamideHCID 178418400CID 53628100

생성물 1

HCID 18630059HCID 18630059, 화합물수율 81%

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
-78 °C

실험 절차

1.3M s-BuLi in cyclohexane (4.8 mL, 6.2 mmol) was added dropwise to a -78° C. cooled solution of the compound of Example e (1.0 g, 4.7 mmol) and TMEDA (930 μL, 6.2 mmol) in THF (15 mL). The resulting yellow mixture was stirred at -78° C. for 45 min, then was quenched by the dropwise addition of trimethyltin chloride (1.41 g, 7.1 mmol) in THF (5 mL), maintaining the internal reaction temperature ≤-65° C. The resulting green solution was warmed to RT to afford a yellow solution which was diluted with ether and extracted twice with aq 10% HCl, and once with sat aq NaHCO3. The ether solution was dried (MgSO4), concentrated, and purified by HPLC with 1:4 ethyl acetate/hexanes to afford 1.37 g of the title compound, an 81% yield, as a colorless oil.

후처리

  1. temperaturemaintaining the internal reaction temperature ≤-65° C
  2. temperatureThe resulting green solution was warmed to RT
  3. customto afford a yellow solution which
  4. extractionextracted twice with aq 10% HCl
  5. dry with materialThe ether solution was dried (MgSO4)
  6. concentrationconcentrated
  7. custompurified by HPLC with 1:4 ethyl acetate/hexanes

출처 및 근거

ORD 기록
ord-0aa593292a3e4a458ab623fa83e7dedb
출처 데이터셋
uspto-grants-2000_10
특허 번호
US06133252

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