tert-Butyl piperazine-1-carboxylate → HCID 59441856, 화합물

HRID 1014254노트

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HRID 1014254 반응식
Br[C:2]1[CH:7]=[C:6]([O:8][CH3:9])[C:5]([N+:10]([O-:12])=[O:11])=[CH:4][C:3]=1[CH3:13].CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.[N:56]1([C:62]([O:64][C:65]([CH3:68])([CH3:67])[CH3:66])=[O:63])[CH2:61][CH2:60][NH:59][CH2:58][CH2:57]1>O1CCOCC1>[CH3:13][C:3]1[CH:4]=[C:5]([N+:10]([O-:12])=[O:11])[C:6]([O:8][CH3:9])=[CH:7][C:2]=1[N:59]1[CH2:58][CH2:57][N:56]([C:62]([O:64][C:65]([CH3:68])([CH3:67])[CH3:66])=[O:63])[CH2:61][CH2:60]1

참가 물질

5

반응물 3

HCID 143452tert-Butyl piperazine-1-carboxylateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 59441753HCID 59441753, 화합물

생성물 1

HCID 59441856HCID 59441856, 화합물수율 38%

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

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온도
60 °C

실험 절차

to a stirred solution of 1-bromo-2-methyl-5-(methyloxy)-4-nitrobenzene (9 g, 36.6 mmol) in 180 mL of Dioxane was added Pd2(dba)2 (2.14 g, 2.34 mmol), XANTPHOS (2.12 g, 3.65 mmol), cesuim carbonte (50 g, 153.6 mmol) and 1,1-dimethylethyl 1-piperazinecarboxylate (13.6 g, 73.15 mmol). The resulting slurry was warmed to 60° C. for 24 hours. The dioxane was removed under reduced pressure and the crude mixture was taken up in ether and filtered to remove cesium carbonate. The ether was, washed with water, dried (Na2SO4), filtered, and rotovaped down. The crude product was purified by flash chromatography to give 1,1-dimethylethyl 4-[2-methyl-5-(methyloxy)-4-nitrophenyl]-1-piperazinecarboxylate (4.83 g, 13.75 mmol, 38%). 1H NMR (400 MHz, CDCl3) δ ppm 7.81 (s, 1 H), 6.56 (s, 1 H), 3.92 (s, 3 H), 3.52-3.63 (m, 4 H), 2.88-2.99 (m, 4 H), 2.25 (s, 3 H), 1.47 (s, 9 H).

후처리

  1. customThe dioxane was removed under reduced pressure
  2. filtrationfiltered
  3. customto remove cesium carbonate
  4. washwashed with water
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. customThe crude product was purified by flash chromatography

출처 및 근거

ORD 기록
ord-9339f2b5f8064d9b9e5581a8ea712246
출처 데이터셋
uspto-grants-2011_07
특허 번호
US07981903B2

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