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N,N'-Dimethylethylenediamine → 2-(4-Chloro-3-(3-hydroxyoxetan-3-yl)pyridin-2-yl)-3,4,6,7,8,9-hexahydropyrazino[1,2-a]indol-1(2H)-one

HRID 1411615
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HRID 1411615 반응식
[C:1]1(=[O:14])[C:6]2=[CH:7][C:8]3[CH2:9][CH2:10][CH2:11][CH2:12][C:13]=3[N:5]2[CH2:4][CH2:3][NH:2]1.Br[C:16]1[C:21]([C:22]2([OH:26])[CH2:25][O:24][CH2:23]2)=[C:20]([Cl:27])[CH:19]=[CH:18][N:17]=1.CNCCNC.CC([O-])=O.[K+]>[Cu]I.O1CCOCC1>[Cl:27][C:20]1[CH:19]=[CH:18][N:17]=[C:16]([N:2]2[CH2:3][CH2:4][N:5]3[C:13]4[CH2:12][CH2:11][CH2:10][CH2:9][C:8]=4[CH:7]=[C:6]3[C:1]2=[O:14])[C:21]=1[C:22]1([OH:26])[CH2:25][O:24][CH2:23]1
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참가 물질

7

반응물 4

HCID 8070N,N'-DimethylethylenediamineHCID 517044Potassium AcetateHCID 580439603,4,6,7,8,9-Hexahydropyrazino[1,2-a]indol-1(2H)-oneHCID 866842603-(2-Bromo-4-chloropyridin-3-yl)oxetan-3-ol

생성물 1

HCID 866842612-(4-Chloro-3-(3-hydroxyoxetan-3-yl)pyridin-2-yl)-3,4,6,7,8,9-hexahydropyrazino[1,2-a]indol-1(2H)-one수율 42%

시약·촉매·용매 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 312751,4-Dioxane용매

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온도
85 °C

실험 절차

A 100 mL single-neck round-bottomed flask equipped with a magnetic stirrer was charged with 3,4,6,7,8,9-hexahydropyrazino[1,2-a]indol-1(2H)-one 101e (190 mg, 1.0 mmol), 148a (795 mg, 3.0 mmol), CuI (95 mg, 0.5 mmol), DMEDA (88 mg, 1.0 mmol), KOAc (294 mg, 3.0 mmol), and 1,4-dioxane (50 ml). The system was evacuated and then refilled with N2. A reflux condenser was attached to the flask, and the reaction mixture was heated at 85° C. for 15 h. Then, the mixture was cooled to room temperature and filtered. The filtrate was concentrated under reduced pressure and the resulting residue was purified by flash column chromatography eluting with 2:1 petroleum ether/ethyl acetate to afford 148b as a yellow solid (156 mg, 42%). MS: [M+H] 374.2.

후처리

  1. customA 100 mL single-neck round-bottomed flask equipped with a magnetic stirrer
  2. customThe system was evacuated
  3. additionrefilled with N2
  4. customA reflux condenser was attached to the flask
  5. temperatureThen, the mixture was cooled to room temperature
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated under reduced pressure
  8. customthe resulting residue was purified by flash column chromatography
  9. washeluting with 2:1 petroleum ether/ethyl acetate

출처 및 근거

ORD 기록
ord-f8a0234fbef640eba64434013c974f09
출처 데이터셋
uspto-grants-2014_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08921353B2

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