Formaldehyde → 1,2,3,4-Tetrahydro-5-(2-chlorobenzyl)-4-methoxymethyl-beta-carboline-3-carboxylic acid ethyl ester

HRID 1720322Notes

Reaction equation

HRID 1720322 reaction equation
[CH2:1]([O:3][C:4](=[O:28])[CH:5]([NH2:27])[CH:6]([C:10]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][C:17]=2[CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[Cl:26])[NH:12][CH:11]=1)[CH2:7][O:8][CH3:9])[CH3:2].[CH2:29]=O.O>C1(C)C=CC=CC=1>[CH2:1]([O:3][C:4]([CH:5]1[CH:6]([CH2:7][O:8][CH3:9])[C:10]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][C:17]=3[CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[Cl:26])[NH:12][C:11]=2[CH2:29][NH:27]1)=[O:28])[CH3:2]

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 962WaterHCID 537537032-Amino-3-[4-(2-chlorobenzyl)-indol-3-yl]-4-methoxybutyric acid ethyl ester

Product 1

HCID 545410741,2,3,4-Tetrahydro-5-(2-chlorobenzyl)-4-methoxymethyl-beta-carboline-3-carboxylic acid ethyl esterYield 19%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

5.2 g (0.013 mol) of 2-amino-3-[4-(2-chlorobenzyl)-indol-3-yl]-4-methoxybutyric acid ethyl ester is refluxed for one hour with 0.44 g of paraformaldehyde in 500 ml of toluene under argon on a water separator. Then it is filtered off from a turbidity. The evaporation residue is chromatographed on silica gel with equal parts of acetone and dichloromethane and yields 1 g (19% of theory) of 1,2,3,4-tetrahydro-5-(2-chlorobenzyl)-4-methoxymethyl-β-carboline-3-carboxylic acid ethyl ester.

Workup

  1. filtrationThen it is filtered off from a turbidity
  2. customThe evaporation residue is chromatographed on silica gel with equal parts of acetone and dichloromethane

Sources & evidence

ORD record
ord-643ed95dd00145089e00456ad4c4487d
Source dataset
uspto-grants-1996_04
Patent number
US05506234

Reaction notes

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