Hydrochloric Acid → (R)-1-Methyl-1,2,3,4-tetrahydroisoquinoline

HRID 2293125Notes

Reaction equation

HRID 2293125 reaction equation
[CH3:1][C@@H:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:5][C:4](=O)[NH:3]1.Cl>O1CCCC1>[CH3:1][C@@H:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:5][CH2:4][NH:3]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 53654348HCID 53654348, compound

Product 1

HCID 11084033(R)-1-Methyl-1,2,3,4-tetrahydroisoquinolineYield 96.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

10.0 g of the compound(62 mM) prepared by Step 2 above and 20 ml of tetrahydrofuran were mixed, and 9 ml of 10.2M borane-methylsulfide complex was dropwise added thereto. The mixture was reacted under reflux for an hour and cooled to room temperature. By adding 10 ml of 6N HCl to the reaction solution, the remaining borane-methylsulfide complex was destroyed and the resultant was neutralized with 10% NaOH. The reaction solution was extracted from ethyl acetate, dehydrated and concentrated to give 8.8 g of the title compound in oil form.

Workup

  1. addition9 ml of 10.2M borane-methylsulfide complex was dropwise added
  2. customThe mixture was reacted
  3. temperatureunder reflux for an hour
  4. customthe remaining borane-methylsulfide complex was destroyed
  5. extractionThe reaction solution was extracted from ethyl acetate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-ce7dea2cf4814d079f997c826411308d
Source dataset
uspto-grants-1997_11
Patent number
US05686458

Reaction notes

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