Sodium borohydride → 1-(4-(Trifluoromethyl)phenyl)-1,2,3,4-tetrahydroisoquinoline

HRID 445255노트

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HRID 445255 반응식
[F:1][C:2]([F:20])([F:19])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH2:12][CH2:11][N:10]=2)=[CH:5][CH:4]=1.[BH4-].[Na+]>CO>[F:20][C:2]([F:1])([F:19])[C:3]1[CH:4]=[CH:5][C:6]([CH:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH2:12][CH2:11][NH:10]2)=[CH:7][CH:8]=1

참가 물질

4

반응물 2

HCID 4311764Sodium borohydrideHCID 57326486HCID 57326486, 화합물

생성물 1

HCID 166406961-(4-(Trifluoromethyl)phenyl)-1,2,3,4-tetrahydroisoquinoline

시약·촉매·용매 1

HCID 887Methanol용매

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온도
0 °C

실험 절차

To a solution of 1-(4-(trifluoromethyl)phenyl)-3,4-dihydroisoquinoline (4.69 g, 17 mmol) in MeOH (24 mL) was added sodium borohydride (1.94 g, 51.1 mmol) slowly at 0° C. Then, the mixture was stirred at 0° C. for 15 min and at RT for 2 h. The solvent was then removed and H2O (20 mL) was added to the residue. A saturated NaHCO3 solution (150 mL) was added slowly and the mixture was extracted with EtOAc (2×200 mL). The combined organic extracts were dried over MgSO4 and concentrated. The residue was mixed with silica gel (4:1; residue:silica gel) and purified by silica gel chromatography (20%-100% EtOAc/hexane) to give the title compound as a white solid. MS (ESI, positive ion) m/z: 278 (M+H).

후처리

  1. customThe solvent was then removed
  2. additionH2O (20 mL) was added to the residue
  3. additionA saturated NaHCO3 solution (150 mL) was added slowly
  4. extractionthe mixture was extracted with EtOAc (2×200 mL)
  5. dry with materialThe combined organic extracts were dried over MgSO4
  6. concentrationconcentrated
  7. additionThe residue was mixed with silica gel (4:1; residue:silica gel)
  8. custompurified by silica gel chromatography (20%-100% EtOAc/hexane)

출처 및 근거

ORD 기록
ord-e915530bbd774fc89c538eff496f0229
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08476297B2

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