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

HRID 518922Notes

Reaction equation

HRID 518922 reaction equation
[CH3:1][C@@H:2]1[CH2:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][N:3]1S(C1C=CC(C)=CC=1)(=O)=O.[Mg]>CO>[CH3:1][C@@H:2]1[CH2:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][NH:3]1

Participants

4

Reactant 2

HCID 5462224MagnesiumHCID 117830978HCID 117830978, compound

Product 1

HCID 7462300(R)-3-Methyl-1,2,3,4-tetrahydroisoquinoline

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 31.15 g (103.15 mmol) of the monotosyl compound obtained in Step B in 500 mL of anhydrous methanol there are added, in portions, 3.92 g (161 mmol) of magnesium turnings. The batch is stirred in the presence of ultrasound for 96 hours. The reaction mixture is then filtered and the solid is washed several times with methanol. The filtrate is then concentrated to dryness. After purification by chromatography over silica gel (dichloromethane/EtOH/NH4OH gradient), the title product is obtained in the form of an oil.

Workup

  1. filtrationThe reaction mixture is then filtered
  2. washthe solid is washed several times with methanol
  3. concentrationThe filtrate is then concentrated to dryness
  4. customAfter purification by chromatography over silica gel (dichloromethane/EtOH/NH4OH gradient)

Sources & evidence

ORD record
ord-a1a5f46354004fb0a2d1fac761edcad7
Source dataset
uspto-grants-2015_08
Patent number
US09115159B2

Reaction notes

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