Borane;tetrahydrofuran → 3-(6-Benzenesulfonyl-1,2,3,4-tetrahydro-naphthalen-1-yl)-propylamine

HRID 339188노트

반응식

HRID 339188 반응식
[C:1]1([S:7]([C:10]2[CH:11]=[C:12]3[C:17](=[CH:18][CH:19]=2)[CH:16]([CH2:20][CH2:21][C:22]#[N:23])[CH2:15][CH2:14][CH2:13]3)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.B.C1COCC1>C1COCC1>[C:1]1([S:7]([C:10]2[CH:11]=[C:12]3[C:17](=[CH:18][CH:19]=2)[CH:16]([CH2:20][CH2:21][CH2:22][NH2:23])[CH2:15][CH2:14][CH2:13]3)(=[O:9])=[O:8])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

참가 물질

4

반응물 2

HCID 2723981Borane;tetrahydrofuranHCID 590217743-(6-Benzenesulfonyl-1,2,3,4-tetrahydro-naphthalen-1-yl)-propionitrile

생성물 1

HCID 590217103-(6-Benzenesulfonyl-1,2,3,4-tetrahydro-naphthalen-1-yl)-propylamine수율 25.4%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

A solution of 3-(6-benzenesulfonyl-1,2,3,4-tetrahydro-naphthalen-1-yl)-propionitrile (0.740 g, 2.27 mmol was dissolved in dry THF, and the reaction mixture was stirred under argon at room temperature. BH3THF (6 mL) was added dropwise, and the reaction mixture was allowed to stir for 15 hours. The reaction mixture was quenched by careful addition of 10% aqueous HCl, followed by stirring for 10 minutes. The reaction mixture was placed under reduced pressure to remove THF. The resulting aqueous solution was diluted with 10 mL of EtOH, made basic by addition of 0.5 M NaOH solution, and warmed to 75° C. for 15 minutes. The solution was cooled and extracted three times with 150 mL of EtOAc. The combined organic layers were washed with water, saturated brine, and dried (MgSO4). Evaporation of the solvent under reduced pressure gave an oil that was purified by elution on silica gel (MeOH:CHCl3 5:95). Removal of the solvent yielded 0.190 g (0.577 mmol, 25.4%) of 3-(6-benzenesulfonyl-1,2,3,4-tetrahydro-naphthalen-1-yl)-propylamine as an oil, which was recrystallized from EtOH/EtOAc as an oxalate salt (0.140 g, 0.334 mmol, 14.7% overall yield). MS: 330 (M+H)+

후처리

  1. stirringto stir for 15 hours
  2. customThe reaction mixture was quenched by careful addition of 10% aqueous HCl
  3. stirringby stirring for 10 minutes
  4. customto remove THF
  5. additionThe resulting aqueous solution was diluted with 10 mL of EtOH
  6. additionmade basic by addition of 0.5 M NaOH solution
  7. temperaturewarmed to 75° C. for 15 minutes
  8. temperatureThe solution was cooled
  9. extractionextracted three times with 150 mL of EtOAc
  10. washThe combined organic layers were washed with water, saturated brine
  11. dry with materialdried (MgSO4)
  12. customEvaporation of the solvent under reduced pressure
  13. customgave an oil that
  14. customwas purified by elution on silica gel (MeOH:CHCl3 5:95)
  15. customRemoval of the solvent

출처 및 근거

ORD 기록
ord-0771f1ba90724860ba33fe5f97edacfd
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08889906B2

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