Water → HCID 54527054, compound

HRID 1740118Notes

Reaction equation

HRID 1740118 reaction equation
[OH:1][CH2:2][CH:3]1[CH2:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:5][NH:4]1.[H-].[Na+].[CH2:15](OS(OCC)(=O)=O)[CH3:16].O>CS(C)=O>[CH2:15]([O:1][CH2:2][C@H:3]1[CH2:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:5][NH:4]1)[CH3:16]

Participants

6

Reactant 4

HCID 962WaterHCID 6163Diethyl SulfateHCID 24758Sodium hydrideHCID 3752277(1,2,3,4-Tetrahydro-isoquinolin-3-yl)-methanol

Product 1

HCID 54527054HCID 54527054, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of 500 mg (3.06 mmol) of (+)-3-hydroxymethyl-1,2,3,4-tetrahydroisoquinoline in 10 mL of DMSO was added 122 mg (3.06 mmol) of NaH (60% in oil) and the mixture was stirred for 45 minutes at room temperature. Then 0.403 mL (3.06 mmol) of diethylsulfate was added via syringe. Foaming occurred and subsided in approximately 15 minutes. The reaction mixture was then stirred at room temperature overnight and poured into water. The product was extracted into ethyl acetate and dried and evaporated to an oil. This was chromatographed on silica gel to give the desired product as an oil, 190 mg. 1H-NMR (CDCl3) δ 1.22 (3H, t, J=7), 2.29 (1H, broad s), 2.55-2.70 (2H, m), 3.09-3.18 (1H, m), 3.41 (1H, t, J=7), 3.50-3.59 (3H, m), 4.06 (2H, ABq, J=5, 21), 7.00-7.13 (4H, m).

Workup

  1. waitsubsided in approximately 15 minutes
  2. stirringThe reaction mixture was then stirred at room temperature overnight
  3. extractionThe product was extracted into ethyl acetate
  4. customdried
  5. customevaporated to an oil
  6. customThis was chromatographed on silica gel

Sources & evidence

ORD record
ord-98c9eed61ed545b1abe6b9c262ac6997
Source dataset
uspto-grants-1999_10
Patent number
US05968944

Reaction notes

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