Tetrahydrofuran → HCID 57904164, compound

HRID 1642116Notes

Reaction equation

HRID 1642116 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([S:9]([N:12]2[CH2:21][CH2:20][C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH:13]2[CH2:22][C:23]([O:25]C)=[O:24])(=[O:11])=[O:10])[CH:5]=[CH:6][C:7]=1[Cl:8].C1COCC1.[OH-].[Na+]>O>[Cl:1][C:2]1[CH:3]=[C:4]([S:9]([N:12]2[CH2:21][CH2:20][C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH:13]2[CH2:22][C:23]([OH:25])=[O:24])(=[O:10])=[O:11])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 66755777HCID 66755777, compound

Product 1

HCID 57904164HCID 57904164, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of methyl 2-(2-(3,4-dichlorophenylsulfonyl)-1,2,3,4-tetrahydroisoquinolin-1-yl)-acetate (14.84 g, 33.2 mmol), THF (200 ml) and water (120 ml) was a and stirred at room temperature. After 4 h, aqueous NaOH solution (6 M, 60 ml) was again added, and stirring was carried out overnight at room temperature. The reaction solution was concentrated under reduced pressure. 6 M HCl solution (125 ml) and DCM (400 ml) were added. After phase separation, the organic phase was washed with saturated NaCl solution, dried (sodium sulfate) and concentrated. For purification, the product was recrystallised from 2-propanol.

Workup

  1. stirringstirring
  2. waitwas carried out overnight at room temperature
  3. concentrationThe reaction solution was concentrated under reduced pressure
  4. addition6 M HCl solution (125 ml) and DCM (400 ml) were added
  5. customAfter phase separation
  6. washthe organic phase was washed with saturated NaCl solution
  7. dry with materialdried (sodium sulfate)
  8. concentrationconcentrated
  9. customFor purification
  10. customthe product was recrystallised from 2-propanol

Sources & evidence

ORD record
ord-bd0e9d9dd32f4ace9f9450f33b931e97
Source dataset
uspto-grants-2012_02
Patent number
US08119633B2

Reaction notes

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