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

HRID 548226Notes

Reaction equation

HRID 548226 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-2783ae78640240b78217f99e0f7fd419
Source dataset
uspto-grants-2011_05
Patent number
US07939666B2

Reaction notes

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