Water → HCID 60064131, compound

HRID 412521Notes

Reaction equation

HRID 412521 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:17][CH2:16][C:15]2[C:10](=[CH:11][C:12]([OH:18])=[CH:13][CH:14]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[CH3:21][S:22][CH2:23]Cl.O>CN(C)C=O>[C:1]([O:5][C:6]([N:8]1[CH2:17][CH2:16][C:15]2[C:10](=[CH:11][C:12]([O:18][CH2:21][S:22][CH3:23])=[CH:13][CH:14]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 962WaterHCID 16916Chloromethyl methyl sulfideHCID 24758Sodium hydrideHCID 10562576Tert-butyl 7-hydroxy-1,2,3,4-tetrahydroisoquinoline-2-carboxylate

Product 1

HCID 60064131HCID 60064131, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 7-hydroxy-1,2,3,4-tetrahydroisoquinoline-2-carboxylic acid tert-butyl ester (13 g) in dirnethylformamide (100 ml) was added 60% sodium hydride (2.5 g) under an argon atmosphere, and the mixture was stirred at room temperature for 30 minutes. Then, chloromethyl methyl sulfide (5.2 ml) was dropwise added with ice-cooling, and the mixture was stirred at room temperature overnight. After completion of the reaction, the reaction mixture was poured into water, extracted with ethyl acetate and washed successively with water and saturated brine. The organic layer was dried over anhydrous sodium sulfate and the solvent was evaporated and the obtained residue was purified by silica gel column chromatography (hexane:acetone=20:1-10:1) and dried under reduced pressure to give the title compound (9.6 g).

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred at room temperature overnight
  3. customAfter completion of the reaction
  4. extractionextracted with ethyl acetate
  5. washwashed successively with water and saturated brine
  6. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  7. customthe solvent was evaporated
  8. customthe obtained residue was purified by silica gel column chromatography (hexane:acetone=20:1-10:1)
  9. customdried under reduced pressure

Sources & evidence

ORD record
ord-03dc22aa97fb456fb5c6ec14aa3dd2b3
Source dataset
uspto-grants-2003_05
Patent number
US06562828B1

Reaction notes

Loading…