Trifluoroacetic acid → 1,2,3,4-Tetrahydro-beta-carboline-9-carboxylic acid 2,2,2-trichloro-ethyl ester

HRID 1582025Notes

Reaction equation

HRID 1582025 reaction equation
[Cl:1][C:2]([Cl:28])([Cl:27])[CH2:3][O:4][C:5]([N:7]1[C:19]2[CH2:18][N:17](C(OC(C)(C)C)=O)[CH2:16][CH2:15][C:14]=2[C:13]2[C:8]1=[CH:9][CH:10]=[CH:11][CH:12]=2)=[O:6].FC(F)(F)C(O)=O>ClCCl>[Cl:28][C:2]([Cl:1])([Cl:27])[CH2:3][O:4][C:5]([N:7]1[C:19]2[CH2:18][NH:17][CH2:16][CH2:15][C:14]=2[C:13]2[C:8]1=[CH:9][CH:10]=[CH:11][CH:12]=2)=[O:6]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 698941943,4-Dihydro-1H-beta-carboline-2,9-dicarboxylic acid 2-tert-butyl ester 9-(2,2,2-trichloro-ethyl) ester

Product 1

HCID 698961661,2,3,4-Tetrahydro-beta-carboline-9-carboxylic acid 2,2,2-trichloro-ethyl esterYield 82.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3,4-Dihydro-1H-β-carboline-2,9-dicarboxylic acid 2-tert-butyl ester 9-(2,2,2-trichloro-ethyl) ester (3.53 g) and trifluoroacetic acid (5 ml) in dichloromethane (30 ml) were stirred at room temperature for 1.5 h. The mixture was partitioned between 6N NaOH solution (70 ml) and dichloromethane (50 ml). The dichloromethane was washed with water (50 ml) and dried (MgSO4) then the solvent removed under reduced pressure to give the title compound (2.25 g, 81%) as a yellow solid.

Workup

  1. customThe mixture was partitioned between 6N NaOH solution (70 ml) and dichloromethane (50 ml)
  2. washThe dichloromethane was washed with water (50 ml)
  3. dry with materialdried (MgSO4)
  4. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-87e6f8bd5b23470d9d661c9177e7951e
Source dataset
uspto-grants-2004_05
Patent number
US06734189B2

Reaction notes

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