Sulfuryl chloride → 7-Chloromethoxy-1,2,3,4-tetrahydroisoquinoline-2-carboxylic acid tert-butyl ester

HRID 412522Notes

Reaction equation

HRID 412522 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:17][CH2:16][C:15]2[C:10](=[CH:11][C:12]([O:18][CH2:19]SC)=[CH:13][CH:14]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].S(Cl)([Cl:25])(=O)=O>C(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[CH2:17][CH2:16][C:15]2[C:10](=[CH:11][C:12]([O:18][CH2:19][Cl:25])=[CH:13][CH:14]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 24648Sulfuryl chlorideHCID 60064131HCID 60064131, compound

Product 1

HCID 600641327-Chloromethoxy-1,2,3,4-tetrahydroisoquinoline-2-carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 7-methylthiomethoxy-1,2,3,4-tetrahydroisoquinoline-2-carboxylic acid tert-butyl ester (9.6 g) in methylene chloride (100 ml) was added a solution of sulfuryl chloride (2.75 ml) in methylene chloride (30 ml) under an argon atmosphere and with ice-cooling, and the mixture was stirred at the same temperature for 1 hour. The solvent was evaporated and toluene was added to the obtained residue to filter off insoluble material. The solvent was evaporated and dried under reduced pressure to give the title compound (7.4 g).

Workup

  1. temperaturewith ice-cooling
  2. customThe solvent was evaporated
  3. additiontoluene was added to the obtained residue
  4. filtrationto filter off insoluble material
  5. customThe solvent was evaporated
  6. customdried under reduced pressure

Sources & evidence

ORD record
ord-ffcfba97d2a34bda87178e46615839da
Source dataset
uspto-grants-2003_05
Patent number
US06562828B1

Reaction notes

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