Potassium Carbonate → Tert-butyl 4-(2-(1-acetylindolin-5-yl)ethyl)piperazine-1-carboxylate

HRID 383820

반응식

HRID 383820 반응식
[N:1]1([C:7]([OH:9])=[O:8])[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.C(=O)([O-])[O-].[K+].[K+].[C:16]([N:19]1[C:27]2[C:22](=[CH:23][C:24]([C:28](=O)[CH2:29]Br)=[CH:25][CH:26]=2)[CH2:21][CH2:20]1)(=[O:18])[CH3:17]>C(#N)C>[C:16]([N:19]1[C:27]2[C:22](=[CH:23][C:24]([CH2:28][CH2:29][N:4]3[CH2:5][CH2:6][N:1]([C:7]([O:9][C:22]([CH3:27])([CH3:23])[CH3:21])=[O:8])[CH2:2][CH2:3]3)=[CH:25][CH:26]=2)[CH2:21][CH2:20]1)(=[O:18])[CH3:17]

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 131766Piperazine-1-carboxylic acidHCID 197113291-(1-acetyl-2,3-dihydro-1H-indol-5-yl)-2-bromoethanone

생성물 1

HCID 59636762Tert-butyl 4-(2-(1-acetylindolin-5-yl)ethyl)piperazine-1-carboxylate수율 55%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

반응 조건

온도
70 °C

실험 절차

To a solution of piperazine-1-carboxylic acid tent-butyl ester (0.750 g, 4.03 mmol) in dry acetonitrile (20 mL) grounded potassium carbonate (0.486 mL, 8.05 mmol) was added followed by the product mixture from Example 38a (1.134 g) and the reaction was heated at 70° C. under argon over night. The acetonitrile was evaporated and DCM and water was added. The layers were separated and the aq phase was extracted with DCM (3×). The combined organic phases were dried (Na2SO4), filtered and evaporated. The crude mixture was purified by flash chromatography (heptane/EtOAc 75/25 to 0/100) to give 0.823 g (55%) of the title compound.

후처리

  1. additionwas added
  2. customThe acetonitrile was evaporated
  3. additionDCM and water was added
  4. customThe layers were separated
  5. extractionthe aq phase was extracted with DCM (3×)
  6. dry with materialThe combined organic phases were dried (Na2SO4)
  7. filtrationfiltered
  8. customevaporated
  9. customThe crude mixture was purified by flash chromatography (heptane/EtOAc 75/25 to 0/100)

출처 및 근거

ORD 기록
ord-f0b72abc57aa416888c498f997519efe
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08367676B2

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