Triethylamine → Ethyl 5-(benzyloxy)-4-(methoxymethyl)-9H-pyrido[3,4-b]indole-3-carboxylate

HRID 236385Notes

Reaction equation

HRID 236385 reaction equation
[CH2:1]([O:3][C:4]([CH:6]1[CH:18]([CH2:19][O:20][CH3:21])[C:17]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][C:15]=3[O:22][CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[NH:10][C:9]=2[CH2:8][NH:7]1)=[O:5])[CH3:2].C(N(CC)CC)C.ClOC(C)(C)C>C(Cl)Cl>[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][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[CH:14]=[CH:13][CH:12]=3)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 8471Triethylamine2×HCID 521297Tert-Butyl hypochloriteHCID 13765246HCID 13765246, compound

Product 1

HCID 123700Ethyl 5-(benzyloxy)-4-(methoxymethyl)-9H-pyrido[3,4-b]indole-3-carboxylateYield 80.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-15 °C

Procedure

10 mmol of 5-benzyloxy-4-methoxymethyl-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid ethyl ester is dissolved in 45 ml of methylene chloride. The solution is cooled to -15° C. and 4.6 ml of triethylamine is added Then a solution of 3.6 ml of tert-butyl hypochlorite in 45 ml of methylene chloride is added within about 10 minutes and stirred for 5 minutes more. After further addition of 3.8 ml of triethylamine, heating to ambient temperature and stirring at this temperature for 4 hours takes place. The solvent is distilled off in vacuum (bath temperature +30° C.) and condensed to dryness at +60° C. bath temperature. The residue is taken up in methylene chloride, filtered over silica gel, rewashed with methylene chloride, the product is eluted with ethyl acetate, the eluate is condensed and washed with ice water. The precipitate is filtered off and wahsed with ice-cold ethyl acetate. 2.93 g of 5-benzyloxy-4-methoxymethyl-β-carboline-3-carboxylic acid ethyl ester (80.5% of theory) with melting point 190.0° C. is obtained.

Workup

  1. temperatureheating to ambient temperature
  2. stirringstirring at this temperature for 4 hours
  3. distillationThe solvent is distilled off in vacuum (bath temperature +30° C.) and condensed to dryness at +60° C. bath temperature
  4. filtrationfiltered over silica gel
  5. washthe product is eluted with ethyl acetate
  6. customcondensed
  7. washwashed with ice water
  8. filtrationThe precipitate is filtered off

Sources & evidence

ORD record
ord-3100059f132148aebab64b767749aaf6
Source dataset
uspto-grants-1987_02
Patent number
US04644062

Reaction notes

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