Water → 2,3,4,4a,9,9a-Hexahydro-1H-carbazole

HRID 2057358

반응식

HRID 2057358 반응식
[CH2:1]1[C:13]2[NH:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH2:4][CH2:3][CH2:2]1.B.C1COCC1.O.[OH-].[Na+]>FC(F)(F)C(O)=O.O1CCCC1>[CH2:1]1[CH:13]2[CH:5]([C:6]3[C:11]([NH:12]2)=[CH:10][CH:9]=[CH:8][CH:7]=3)[CH2:4][CH2:3][CH2:2]1

참가 물질

7

반응물 4

HCID 962WaterHCID 136641,2,3,4-TetrahydrocarbazoleHCID 14798Sodium HydroxideHCID 2723981Borane;tetrahydrofuran

생성물 1

HCID 1011622,3,4,4a,9,9a-Hexahydro-1H-carbazole수율 80%

시약·촉매·용매 2

HCID 6422Trifluoroacetic acid용매HCID 8028Tetrahydrofuran용매

실험 절차

1,2,3,4-Tetrahydrocarbazole (75 milligrams) was dissolved under nitrogen in 3 milliliters of trifluoroacetic acid. To the mixture, cooled in a water bath, was added dropwise about 1.5 milliliters of an about 1 M BH3.THF in tetrahydrofuran. The mixture was stirred at room temperature for about 45 minutes. Thereafter, water (1 milliliter) was added slowly and the resulting solution stirred for 10 minutes. The solution was then made basic with 10 percent aqueous sodium hydroxide, and the basic solution extracted with methylene chloride. The organic methylene chloride layer was washed once with saturated sodium chloride, dried over potassium carbonate, and evaporated in vacuo to obtain 60 milligrams (80 percent yield) of a crystalline 1,2,3,4,4a,9a-hexahydrocarbazole product, m.p., 93°-96° C.

후처리

  1. temperatureTo the mixture, cooled in a water bath
  2. stirringthe resulting solution stirred for 10 minutes
  3. extractionthe basic solution extracted with methylene chloride
  4. washThe organic methylene chloride layer was washed once with saturated sodium chloride
  5. dry with materialdried over potassium carbonate
  6. customevaporated in vacuo

출처 및 근거

ORD 기록
ord-04c9230717ec428d9d3763e4efae0d9a
출처 데이터셋
uspto-grants-1980_07
특허 번호
US04210590

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