Water → HCID 60064133, compound

HRID 412530Notes

Reaction equation

HRID 412530 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:20][CH2:19][C:18]2[C:13](=[CH:14][C:15]([OH:21])=[CH:16][CH:17]=2)[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[CH3:24][S:25][CH2:26]Cl.O>CN(C)C=O>[CH2:1]([O:8][C:9]([N:11]1[CH2:20][CH2:19][C:18]2[C:13](=[CH:14][C:15]([O:21][CH2:24][S:25][CH3:26])=[CH:16][CH:17]=2)[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 16916Chloromethyl methyl sulfideHCID 24758Sodium hydrideHCID 11254587Benzyl 7-hydroxy-3,4-dihydroisoquinoline-2(1H)-carboxylate

Product 1

HCID 60064133HCID 60064133, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 7-hydroxy-1,2,3,4-tetrahydroisoquinoline-2-carboxylic acid benzyl ester (2.5 g) in dimethylformamide (25 ml) was added 60% sodium hydride (390 mg) with ice-cooling and under an argon atmosphere, and the mixture was stirred at the same temperature for 30 min. Then, chloromethyl methyl sulfide (0.96 ml) was added, and the mixture was stirred at room temperature for 12 hours. After completion of the reaction, water was added and the mixture was extracted with ethyl acetate and washed with water. The organic layer was dried over anhydrous sodium sulfate and the solvent was evaporated. The obtained oil was purified by silica gel column chromatography (hexane:ethyl acetate=8:1) and dried under reduced pressure to give the title compound (2.7 g).

Workup

  1. temperaturecooling and under an argon atmosphere
  2. stirringthe mixture was stirred at room temperature for 12 hours
  3. additionwas added
  4. extractionthe mixture was extracted with ethyl acetate
  5. washwashed with water
  6. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  7. customthe solvent was evaporated
  8. customThe obtained oil was purified by silica gel column chromatography (hexane:ethyl acetate=8:1)
  9. customdried under reduced pressure

Sources & evidence

ORD record
ord-129f941f09794045b214a68317f1efab
Source dataset
uspto-grants-2003_05
Patent number
US06562828B1

Reaction notes

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