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Sodium borohydride → Rac-8-trifluoromethoxy-1,2,3,4,10,10a-hexahydro-pyrazino[1,2-a]indole

HRID 2223496
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HRID 2223496 반응식
[F:1][C:2]([F:18])([F:17])[O:3][C:4]1[CH:12]=[CH:11][C:10]2[N:9]3[CH2:13][CH2:14][NH:15][CH2:16][C:8]3=[CH:7][C:6]=2[CH:5]=1.[BH4-].[Na+]>C1COCC1.C(O)(C(F)(F)F)=O>[F:18][C:2]([F:1])([F:17])[O:3][C:4]1[CH:12]=[CH:11][C:10]2[N:9]3[CH2:13][CH2:14][NH:15][CH2:16][CH:8]3[CH2:7][C:6]=2[CH:5]=1
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참가 물질

5

반응물 2

HCID 4311764Sodium borohydrideHCID 685320458-Trifluoromethoxy-1,2,3,4-tetrahydro-pyrazino[1,2-a]indole

생성물 1

HCID 68531143Rac-8-trifluoromethoxy-1,2,3,4,10,10a-hexahydro-pyrazino[1,2-a]indole수율 76%

시약·촉매·용매 2

HCID 6422Trifluoroacetic acid용매HCID 8028Tetrahydrofuran용매

실험 절차

To 8-trifluoromethoxy-1,2,3,4-tetrahydro-pyrazino[1,2-a]indole (0.41 g) in THF (2.2 mL) and TFA (4.4 mL) at 0° C. was added portion wise sodium borohydride (0.124 g). The reaction mixture was allowed to warm up to room temperature and stirred for 35 minutes. After such time, the reaction mixture was concentrated in vacuo, and the residue was dissolved in dichloromethane and poured over water. A sodium hydroxide solution (10 M) was the added until reaching pH 13.5. After 15 minutes, the phases were separated. The aqueous phase was extracted with dichloromethane twice. The combined organic layers were then washed with brine, dried with magnesium sulfate, concentrated in vacuo and purified by column chromatography to yield the title compound (0.31 g, 76%).

후처리

  1. concentrationAfter such time, the reaction mixture was concentrated in vacuo
  2. dissolutionthe residue was dissolved in dichloromethane
  3. additionpoured over water
  4. additionadded
  5. waitAfter 15 minutes
  6. customthe phases were separated
  7. extractionThe aqueous phase was extracted with dichloromethane twice
  8. washThe combined organic layers were then washed with brine
  9. dry with materialdried with magnesium sulfate
  10. concentrationconcentrated in vacuo
  11. custompurified by column chromatography

출처 및 근거

ORD 기록
ord-5f7d114bb1f243a9a8cb44728396bbc8
출처 데이터셋
uspto-grants-2008_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07375226B2

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