Trifluoroacetic acid → 9-methyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole

HRID 864479Notes

Reaction equation

HRID 864479 reaction equation
FC(F)(F)C(O)=O.C(OC([N:15]1[CH2:27][CH2:26][C:25]2[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[N:18]([CH3:28])[C:17]=2[CH2:16]1)=O)(C)(C)C>ClCCl>[CH3:28][N:18]1[C:19]2[C:24](=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:25]2[CH2:26][CH2:27][NH:15][CH2:16][C:17]1=2

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Trifluoroacetic acid (3.5 ml, 45.23 mmol) was added to a solution of 2-t-butoxycarbonyl-9-methyl-1,2,3,4-tetrahydropyrido[3,4-b]indole (1.848 g, 6.461 mmol) in dichloromethane (25 ml) and stirred at room temperature for 3 hours, diluted with dichloromethane (125 ml), washed with 2M sodium hydroxide (2×50 ml), water and dried (MgSO4). The magnesium sulfate was collected by filtration and the filtrate evaporated in vacuo to give the title product.

Workup

  1. washwashed with 2M sodium hydroxide (2×50 ml), water
  2. dry with materialdried (MgSO4)
  3. filtrationThe magnesium sulfate was collected by filtration
  4. customthe filtrate evaporated in vacuo

Sources & evidence

ORD record
ord-32b30312f40747f2b8e8d51b50178de1
Source dataset
uspto-grants-1996_10
Patent number
US05563147

Reaction notes

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