Trifluoroacetic acid → 3-(Indol-2-yl)-8-methyl-8-azabicyclo[3.2.1]oct-2-ene

HRID 1871915Notes

Reaction equation

HRID 1871915 reaction equation
O[C:2]1([C:11]2[N:12](S(C3C=CC=CC=3)(=O)=O)[C:13]3[C:18]([CH:19]=2)=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH2:8][CH:7]2[N:9]([CH3:10])[CH:4]([CH2:5][CH2:6]2)[CH2:3]1.FC(F)(F)C(O)=O>ClCCl>[NH:12]1[C:13]2[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:19]=[C:11]1[C:2]1[CH2:8][CH:7]2[N:9]([CH3:10])[CH:4]([CH2:5][CH2:6]2)[CH:3]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 186898593-Hydroxy-3-(1-phenylsulfonylindol-2-yl)-8-methyl-8-azabicyclo[3.2.1]octane

Product 1

HCID 186898983-(Indol-2-yl)-8-methyl-8-azabicyclo[3.2.1]oct-2-ene

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 3-hydroxy-3-(1-phenylsulfonylindol-2-yl)-8-methyl-8-azabicyclo[3.2.1]octane and trifluoroacetic acid in dichloromethane is stirred at room temperature until the dehydration is complete. The reaction mixture is concentrated under reduced pressure and the residue partitioned between dichloromethane and saturated aqueous sodium bicarbonate. The organic phase is separated, washed well with water, washed with saturated aqueous sodium chloride, dried over magnesium sulfate and concentrated under reduced pressure to provide the desired compound.

Workup

  1. concentrationThe reaction mixture is concentrated under reduced pressure
  2. customthe residue partitioned between dichloromethane and saturated aqueous sodium bicarbonate
  3. customThe organic phase is separated
  4. washwashed well with water
  5. washwashed with saturated aqueous sodium chloride
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-07d74af8c5074b028d5c2a341f984aec
Source dataset
uspto-grants-2000_08
Patent number
US06107307

Reaction notes

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