Isopropanol → 5-Hydroxymethyl-4-methoxymethyl-beta-carboline-3-carboxylic acid isopropyl ester

HRID 569083Notes

Reaction equation

HRID 569083 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][OH:23])[CH:14]=[CH:13][CH:12]=3)=[O:5])[CH3:2].[CH:24](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][OH:23])[CH:14]=[CH:13][CH:12]=3)=[O:5])([CH3:24])[CH3:2]

Participants

4

Reactant 2

HCID 3776IsopropanolHCID 138503635-Hydroxymethyl-4-methoxymethyl-beta-carboline-3-carboxylic acid ethyl ester

Product 1

HCID 544935095-Hydroxymethyl-4-methoxymethyl-beta-carboline-3-carboxylic acid isopropyl ester

Reagents, catalysts & solvents 1

HCID 11026Titanium isopropoxideCatalyst

Procedure

5-Hydroxymethyl-4-methoxymethyl-beta-carboline-3-carboxylic acid ethyl ester (7.27 g) is refluxed in isopropanol (1000 ml) with titanium tetraisopropylate (7.1 ml) for 5 hours. The solution is evaporated, the residue is dissolved in ethyl acetate. The complete solution is reached by addition of 1N hydrochloric acid. Then it is made alkaline by addition of 1N sodium hydroxide solution. A precipitate resulting thereby is suctioned off. The filtrate is evaporated and yields a residue of 6.0 g of the title compound.

Workup

  1. customThe solution is evaporated
  2. dissolutionthe residue is dissolved in ethyl acetate
  3. additionThe complete solution is reached by addition of 1N hydrochloric acid
  4. additionby addition of 1N sodium hydroxide solution
  5. customA precipitate resulting
  6. customThe filtrate is evaporated

Sources & evidence

ORD record
ord-3e2f5e25ea5b4862a49d9c3538f91032
Source dataset
uspto-grants-1988_03
Patent number
US04731365

Reaction notes

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