Hydrochloric Acid → 2,3,4,9-Tetrahydro-1H-beta-carboline-1-carboxylic acid methyl ester

HRID 2276967Notes

Reaction equation

HRID 2276967 reaction equation
[CH:1]1([C:14]([OH:16])=[O:15])[C:13]2[NH:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH2:4][CH2:3][NH:2]1.Cl.[CH3:18]O>>[CH3:18][O:15][C:14]([CH:1]1[C:13]2[NH:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH2:4][CH2:3][NH:2]1)=[O:16]

Participants

4

Reactant 3

HCID 313Hydrochloric Acid2×HCID 887MethanolHCID 1458792,3,4,9-Tetrahydro-1H-pyrido(3,4-b)indole-1-carboxylic acid

Product 1

HCID 103765542,3,4,9-Tetrahydro-1H-beta-carboline-1-carboxylic acid methyl ester

Procedure

A solution of tetrahydro-beta-carboline-1-carboxylic acid (7.4 g) in MeOH (250 ml) was saturated with HCl gas for 20 min. The reaction mixture was gently stirred at room temperature for 18 h. and ca. 80% conversion was observed. The reaction mixture was re-treated with HCl gas and allowed to stir for another 18 h. Upon completion of the reaction the mixture was concentrated in vacuo to yield 2,3,4,9-tetrahydro-1H-beta-carboline-1-carboxylic acid methyl ester (building block C), LCMS purity 95%, m/z 231 [M++H]+. The product was used without further purification.

Workup

  1. stirringto stir for another 18 h
  2. customUpon completion of the reaction the mixture
  3. concentrationwas concentrated in vacuo

Sources & evidence

ORD record
ord-e9c8c9d0114c41108b51f3cd0fef77e8
Source dataset
uspto-grants-2015_09
Patent number
US09133104B2

Reaction notes

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