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

HRID 2057358

Reaction equation

HRID 2057358 reaction equation
[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

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 6422Trifluoroacetic acidSolventHCID 8028TetrahydrofuranSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-04c9230717ec428d9d3763e4efae0d9a
Source dataset
uspto-grants-1980_07
Patent number
US04210590

Linked notes

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