Hydrochloric Acid → Methyl L-1,2,3,4-tetrahydroisoquinoline-3-carboxylate

HRID 2289173Notes

Reaction equation

HRID 2289173 reaction equation
[CH2:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][C@@H:3]([C:11]([OH:13])=[O:12])[NH:2]1.[CH3:14]OC(OC)OC.Cl>CO>[CH2:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][C@@H:3]([C:11]([O:13][CH3:14])=[O:12])[NH:2]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 9005Trimethyl orthoformateHCID 2733226(-)-1,2,3,4-Tetrahydroisoquinoline-3-carboxylic acid

Product 1

HCID 2760579Methyl L-1,2,3,4-tetrahydroisoquinoline-3-carboxylate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 1 eq. of (S)-1,2,3,4-tetrahydro-3-isoquinolinecarboxylic acid (Aldrich Chemical Co., Milwaukee, Wis.), 5 eq. of trimethylorthoformate, methanol and catalytic HCl were allowed to heat at reflux for 5 h. Concentration in vacuo provided methyl (S)-1,2,3,4-tetrahydro-3-isoquinolinecarboxylate.

Workup

  1. temperatureto heat
  2. temperatureat reflux for 5 h
  3. concentrationConcentration in vacuo

Sources & evidence

ORD record
ord-79ad8340afd146e38ac4bd802f82877e
Source dataset
uspto-grants-2000_07
Patent number
US06090950

Reaction notes

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