Sodium Hydroxide → 3,4-Dihydro-1H-beta-carboline-2,9-dicarboxylic acid 2-tert-butyl ester 9-(2,2,2-trichloro-ethyl) ester

HRID 992414Notes

Reaction equation

HRID 992414 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:20][CH2:19][C:18]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[NH:11][C:10]=2[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Cl:21][C:22]([Cl:29])([Cl:28])[CH2:23][O:24][C:25](Cl)=[O:26].[OH-].[Na+]>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.ClCCl>[Cl:21][C:22]([Cl:29])([Cl:28])[CH2:23][O:24][C:25]([N:11]1[C:10]2[CH2:9][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[CH2:20][CH2:19][C:18]=2[C:17]2[C:12]1=[CH:13][CH:14]=[CH:15][CH:16]=2)=[O:26]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 870632,2,2-Trichloroethyl chloroformateHCID 18377349tert-butyl 3,4-dihydro-1H-pyrido[3,4-b]indole-2(9H)-carboxylate

Product 1

HCID 698941943,4-Dihydro-1H-beta-carboline-2,9-dicarboxylic acid 2-tert-butyl ester 9-(2,2,2-trichloro-ethyl) esterYield 28%

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 6344DichloromethaneSolvent2×

Procedure

1,3,4,9-Tetrahydro-β-carboline-2-carboxylic acid tert-butyl ester (7.68 g), 2,2,2-trichloroethylchloroformate (5.8 ml), sodium hydroxide (2.8 g) and tetrabutylammonium iodide (catalytic) in dichloromethane (100 ml) were stirred under nitrogen at room temperature for 5 h. The mixture was diluted with dichloromethane (100 ml), washed with water (150 ml) and brine (100 ml), then dried (MgSO4) and the solvent removed under reduced pressure. The residue was chromatographed (SiO2, 1% methanol in dichloromethane) to give the title compound (3.53 g, 28%) as a yellow foam.

Workup

  1. washwashed with water (150 ml) and brine (100 ml)
  2. dry with materialdried (MgSO4)
  3. customthe solvent removed under reduced pressure
  4. customThe residue was chromatographed (SiO2, 1% methanol in dichloromethane)

Sources & evidence

ORD record
ord-de1e37f8d1ba453f964b7a769b225baa
Source dataset
uspto-grants-2002_10
Patent number
US06469020B2

Reaction notes

Loading…