Isopropanol → Abecarnil

HRID 36333Notes

Reaction equation

HRID 36333 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])=[CH:15][C:14]([O:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[CH:13][CH:12]=3)=[O:5])[CH3:2].[CH:30](O)(C)C>CC(C)[O-].CC(C)[O-].CC(C)[O-].CC(C)[O-].[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])=[CH:15][C:14]([O:22][CH2:23][C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1)=[CH:13][CH:12]=3)=[O:5])([CH3:30])[CH3:2]

Participants

4

Reactant 2

HCID 3776IsopropanolHCID 121926Ethyl 4-(methoxymethyl)-6-(phenylmethoxy)-9H-pyrido(3,4-b)indole-3-carboxylate

Product 1

HCID 65914AbecarnilYield 80%

Reagents, catalysts & solvents 1

HCID 11026Titanium isopropoxideCatalyst

Procedure

1.4 g (3.6 mmol) of 6-benzyloxy-4-methoxymethyl-β-carboline-3-carboxylic acid ethyl ester is boiled under reflux for 2 hours in 100 ml of isopropanol with 0.7 ml (2.2 mmol) of titanium tetraisopropoxide. After concentration, the mixture is taken up in 80 ml of 1N hydrochloric acid and extracted by shaking with 250 ml of ethyl acetate. The ethyl acetate phase is washed with a small amount of water, dried, filtered, and concentrated. After chromatography over silica gel with methylene chloride:acetone=4:1 as the eluent, the 6-benzyloxy-4-methoxymethyl-β-carboline-3-carboxylic acid isopropyl ester, mp 150°-151° C., is obtained in an 80% yield.

Workup

  1. concentrationAfter concentration
  2. extractionextracted
  3. washThe ethyl acetate phase is washed with a small amount of water
  4. customdried
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-57ab955ead564d74b68b1432da8da289
Source dataset
uspto-grants-1995_05
Patent number
US05414002

Reaction notes

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