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

HRID 2166366Notes

Reaction equation

HRID 2166366 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]([O:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[CH:14]=[CH:13][CH:12]=3)=[O:5])[CH3:2].[CH:29](O)(C)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]([O:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[CH:14]=[CH:13][CH:12]=3)=[O:5])([CH3:29])[CH3:2]

Participants

4

Reactant 2

HCID 3776IsopropanolHCID 138000715-Phenoxy-4-methoxymethyl-beta-carboline-3-carboxylic acid ethyl ester

Product 1

HCID 138001015-Phenoxy-4-methoxymethyl-beta-carboline-3-carboxylic acid isopropyl esterYield 82%

Reagents, catalysts & solvents 1

HCID 114942Titanium cation (4+)Catalyst

Procedure

540 mg of 5-phenoxy-4-methoxymethyl-beta-carboline-3-carboxylic acid ethyl ester in 30 ml of isopropanol is refluxed with 0.2 ml of titanium(IV) isopropylate for 2 hours. After concentration, it is mixed with 0.5N hydrochloric acid and extracted with ethyl acetate. The ethyl acetate phase is dried, filtered and concentrated and digested with diisopropyl ether. 450 mg (82% of theory) of 5-phenoxy-4-methoxymethyl-beta-carboline-3-carboxylic acid isopropyl ester with a melting point of 207°-209° C. is obtained.

Workup

  1. concentrationAfter concentration, it
  2. additionis mixed with 0.5N hydrochloric acid
  3. extractionextracted with ethyl acetate
  4. dry with materialThe ethyl acetate phase is dried
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-b74cf49a576c4185baf6b4e3477a2c00
Source dataset
uspto-grants-1990_07
Patent number
US04945090

Reaction notes

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