Tributyltin Chloride → 1-Methyl-4-((4-(tributylstannyl)furan-2-yl)methyl)piperazine

HRID 2241269

반응식

HRID 2241269 반응식
Br[C:2]1[CH:3]=[C:4]([CH2:7][N:8]2[CH2:13][CH2:12][N:11]([CH3:14])[CH2:10][CH2:9]2)[O:5][CH:6]=1.C([Li])(C)(C)C.[CH2:20]([Sn:24]([CH2:30][CH2:31][CH2:32][CH3:33])([CH2:26][CH2:27][CH2:28][CH3:29])Cl)[CH2:21][CH2:22][CH3:23]>C1COCC1>[CH3:14][N:11]1[CH2:12][CH2:13][N:8]([CH2:7][C:4]2[O:5][CH:6]=[C:2]([Sn:24]([CH2:26][CH2:27][CH2:28][CH3:29])([CH2:30][CH2:31][CH2:32][CH3:33])[CH2:20][CH2:21][CH2:22][CH3:23])[CH:3]=2)[CH2:9][CH2:10]1

참가 물질

5

반응물 3

HCID 15096Tributyltin ChlorideHCID 160991801-((4-Bromofuran-2-yl)methyl)-4-methylpiperazineHCID 178418306HCID 178418306, 화합물

생성물 1

HCID 685132471-Methyl-4-((4-(tributylstannyl)furan-2-yl)methyl)piperazine수율 21.3%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
-78 °C

실험 절차

A stirred mixture of 1-((4-bromofuran-2-yl)methyl)-4-methylpiperazine (2.10 g, 8.10 mmol) and THF (50 mL) was cooled to −78° C. in a dry ice/acetone bath. tert-Butyllithium (7.60 mL, 12.2 mmol; 1.6 M in pentane) was added and the reaction mixture was stirred for 30 minutes. Next, tributylchlorostannane (2.09 ml, 7.70 mmol) was added and the reaction mixture was stirred for 30 minutes. The reaction was quenched by addition of pH 7 phosphate buffer (20 mL) and warming to room temperature. The mixture was extracted with diethyl ether, dried over sodium sulfate, filtered and concentrated. The crude material was purified on a Biotage 40S column, eluting with 1:1 EtOAc/hexanes (500 mL), 2:1 EtOAc/hexanes (500 mL), then EtOAc (1 L) to provide a product mixture as a light yellow oil (0.77 g, 86:14 ratio of 1-((4-bromo-5-(tributylstannyl)furan-2-yl)methyl)-4-methylpiperazine to 1-methyl-4-((4-(tributylstannyl)furan-2-yl)methyl)piperazine by 1H-NMR). The mixture was carried forward without separation at this step.

후처리

  1. stirringthe reaction mixture was stirred for 30 minutes
  2. customThe reaction was quenched by addition of pH 7 phosphate buffer (20 mL)
  3. temperaturewarming to room temperature
  4. extractionThe mixture was extracted with diethyl ether
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude material was purified on a Biotage 40S column
  9. washeluting with 1:1 EtOAc/hexanes (500 mL), 2:1 EtOAc/hexanes (500 mL)

출처 및 근거

ORD 기록
ord-14f4b5fc9e8a43ab8e4306a2a1df8cfc
출처 데이터셋
uspto-grants-2010_05
특허 번호
US07723330B2

연결된 노트

불러오는 중…