Boron trifluoride etherate → 2-Benzyl-6-nitro-1,2,3,4-tetrahydroisoquinoline

HRID 1954426노트

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HRID 1954426 반응식
[BH4-].[Na+].B(F)(F)F.CCOCC.[CH2:12]([N:19]1[C:28](=O)[CH2:27][C:26]2[C:21](=[CH:22][CH:23]=[C:24]([N+:30]([O-:32])=[O:31])[CH:25]=2)[C:20]1=O)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[OH-].[Na+]>C1COCC1>[CH2:12]([N:19]1[CH2:28][CH2:27][C:26]2[C:21](=[CH:22][CH:23]=[C:24]([N+:30]([O-:32])=[O:31])[CH:25]=2)[CH2:20]1)[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

참가 물질

6

반응물 4

HCID 8000Boron trifluoride etherateHCID 14798Sodium HydroxideHCID 4311764Sodium borohydrideHCID 232961796-Nitro-2-(phenylmethyl)-1,3(2H,4H)-isoquinolinedione

생성물 1

HCID 222696172-Benzyl-6-nitro-1,2,3,4-tetrahydroisoquinoline수율 104.3%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

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온도
25 °C

실험 절차

To a suspension of sodium borohydride (2.13 g, 56.2 mmole) in THF (56 mL) at 0° C. was added boron trifluoride etherate (9 mL, 73 mmole) dropwise. After stirring the contents for 1 hr., dione (16) (5.0 g, 16.9 mmole) in THF (150 mL) was added at 0° C. over a period of 1.5 hr. The contents were warmed to 25° C. for 30 min. and then refluxed for 16 hr. The completed reaction was cooled to 0° C. and cautiously quenched with aqueous 1N sodium hydroxide (75 mL, 75 mmole) while maintaining the temperature at approximately 9° C. The quenched reaction was stirred for 30 min. at 0° C., 1 hr. at 25° C., 50° C. for 18 hrs. and then cooled to 20° C. The solvents were removed under vacuum, ethyl acetate (100 mL) was added and the layers separated. The organic layer was washed with brine, treated with sodium sulfate and the solvents removed under vacuum to afford 4.73 g of a light brown oil which was of sufficient purity to employ in the next step.

후처리

  1. temperaturerefluxed for 16 hr
  2. customThe completed reaction
  3. temperaturewas cooled to 0° C.
  4. temperaturewhile maintaining the temperature at approximately 9° C
  5. customThe quenched reaction
  6. stirringwas stirred for 30 min. at 0° C., 1 hr
  7. waitat 25° C., 50° C. for 18 hrs
  8. temperatureand then cooled to 20° C
  9. customThe solvents were removed under vacuum, ethyl acetate (100 mL)
  10. additionwas added
  11. customthe layers separated
  12. washThe organic layer was washed with brine
  13. additiontreated with sodium sulfate
  14. customthe solvents removed under vacuum

출처 및 근거

ORD 기록
ord-a87e9bf2683843f6964dcfba3f2aeed2
출처 데이터셋
uspto-grants-2000_09
특허 번호
US06121283

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