Potassium Carbonate → 3-[2-((R)-6,8-Dichloro-2-methyl-1,2,3,4-tetrahydroisoquinolin-4-yl)phenyl]-oxazolidine-2,4-dione

HRID 251872Notes

Reaction equation

HRID 251872 reaction equation
[C:1]([O:4][CH2:5][C:6](=[O:27])[NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[C@H:14]1[C:23]2[C:18](=[C:19]([Cl:25])[CH:20]=[C:21]([Cl:24])[CH:22]=2)[CH2:17][N:16]([CH3:26])[CH2:15]1)(=[O:3])C.C(=O)([O-])[O-].[K+].[K+]>CO>[Cl:24][C:21]1[CH:22]=[C:23]2[C:18](=[C:19]([Cl:25])[CH:20]=1)[CH2:17][N:16]([CH3:26])[CH2:15][C@H:14]2[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=1[N:7]1[C:6](=[O:27])[CH2:5][O:4][C:1]1=[O:3]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 59682852[2-((R)-6,8-Dichloro-2-methyl-1,2,3,4-tetrahydroisoquinolin-4-yl)phenyl-carbamoyl]methyl acetate

Product 1

HCID 117180843-[2-((R)-6,8-Dichloro-2-methyl-1,2,3,4-tetrahydroisoquinolin-4-yl)phenyl]-oxazolidine-2,4-dioneYield 92.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

[2-((R)-6,8-Dichloro-2-methyl-1,2,3,4-tetrahydroisoquinolin-4-yl)phenyl-carbamoyl]methyl acetate (180 mg) was dissolved in methanol (5 ml). With stirring, potassium carbonate (305 mg, finely powdered) was added and the mixture was then stirred efficiently at room temperature for 4 h. Subsequently, the solvent was evaporated off, and the residue was taken up in ethyl acetate and washed three times with water. The ethyl acetate phase was dried with magnesium sulfate, filtered and concentrated. 160 mg of the desired product were obtained.

Workup

  1. stirringthe mixture was then stirred efficiently at room temperature for 4 h
  2. customSubsequently, the solvent was evaporated off
  3. washwashed three times with water
  4. dry with materialThe ethyl acetate phase was dried with magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-6c393ce93aae4bb58c583c04b60453a1
Source dataset
uspto-grants-2011_01
Patent number
US07868003B2

Reaction notes

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