Trifluoroacetic acid → Trifluoroacetate

HRID 2301078Notes

Reaction equation

HRID 2301078 reaction equation
C1(OC)C=CC=CC=1.[F:9][C:10]([F:15])([F:14])[C:11]([OH:13])=[O:12].C(OC([N:23]1[CH2:35][CH2:34][C:33]2[C:32]3[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=3)[N:26]([CH3:36])[C:25]=2[CH2:24]1)=O)(C)(C)C>ClCCl>[CH3:36][N:26]1[C:27]2[C:32](=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:33]2[CH2:34][CH2:35][NH:23][CH2:24][C:25]1=2.[F:9][C:10]([F:15])([F:14])[C:11]([O-:13])=[O:12]

Participants

6

Reactant 3

HCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 10989795tert-Butyl 9-methyl-3,4-dihydro-1H-pyrido[3,4-b]indole-2(9H)-carboxylate

Product 2

HCID 84468TrifluoroacetateHCID 109977549-methyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A 1 ml portion of anisole and 0.7 ml of trifluoroacetic acid were added to 7 ml of dichloromethane solution containing 200 mg (0.70 mmol) portion of 2-t-butoxycarbonyl-9-methyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole and stirred at room temperature for 4 hours. The solvent was removed by evaporation under a reduced pressure and the residue was recrystallized from acetone-diisopropyl ether to obtain 9-methyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole quantitatively as trifluoroacetate.

Workup

  1. customThe solvent was removed by evaporation under a reduced pressure
  2. customthe residue was recrystallized from acetone-diisopropyl ether

Sources & evidence

ORD record
ord-f1e2d0244b354d5b839f24783132a194
Source dataset
uspto-grants-2002_12
Patent number
US06498251B1

Reaction notes

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