Isopropanol → 5-(2-Chlorobenzyl)-4-methoxymethyl-beta-carboline-3-carboxylic acid isopropyl ester

HRID 1720325Notes

Reaction equation

HRID 1720325 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:7]=[CH:8][C:9]2[NH:10][C:11]3[C:16]([C:17]=2[C:18]=1[CH2:19][O:20][CH3:21])=[C:15]([CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[Cl:29])[CH:14]=[CH:13][CH:12]=3)=[O:5])[CH3:2].[CH:30](O)(C)C>CC([O-])C.CC([O-])C.CC([O-])C.CC([O-])C.[Ti+4]>[CH:1]([O:3][C:4]([C:6]1[N:7]=[CH:8][C:9]2[NH:10][C:11]3[C:16]([C:17]=2[C:18]=1[CH2:19][O:20][CH3:21])=[C:15]([CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[Cl:29])[CH:14]=[CH:13][CH:12]=3)=[O:5])([CH3:30])[CH3:2]

Participants

4

Reactant 2

HCID 3776IsopropanolHCID 53662264HCID 53662264, compound

Product 1

HCID 536421005-(2-Chlorobenzyl)-4-methoxymethyl-beta-carboline-3-carboxylic acid isopropyl ester

Reagents, catalysts & solvents 1

HCID 11026Titanium isopropoxideCatalyst

Procedure

0.2 g (5 mmol) of 5-(2-chlorobenzyl)-4-methoxymethyl-β-carboline-3-carboxylic acid ethyl ester is refluxed for 2 hours in 35 ml of isopropanol with 0.15 ml (0.5 mmol) of titanium tetraisopropylate. The mixture is filtered and the filtrate concentrated by evaporation to approximately a third. 0.112 g (54% of theory) of 5-(2-chlorobenzyl)-4-methoxymethyl-β-carboline-3-carboxylic acid isopropyl ester crystallizes out, melting point 187°-189° C.

Workup

  1. filtrationThe mixture is filtered
  2. concentrationthe filtrate concentrated by evaporation to approximately a third
  3. custom0.112 g (54% of theory) of 5-(2-chlorobenzyl)-4-methoxymethyl-β-carboline-3-carboxylic acid isopropyl ester crystallizes out

Sources & evidence

ORD record
ord-e355a2a6d0f94ded808bf248e2a27ad6
Source dataset
uspto-grants-1996_04
Patent number
US05506234

Reaction notes

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