Thiophenol → HCID 69053351, compound

HRID 2100624Notes

Reaction equation

HRID 2100624 reaction equation
C[O:2][C:3]1[CH:12]=[C:11]([CH3:13])[C:10]2[C:9](=[O:14])[NH:8][C@@H:7]3[CH2:15][N:16]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:17][C@H:6]3[C:5]=2[CH:4]=1.C1(S)C=CC=CC=1.C(=O)([O-])[O-].[K+].[K+]>CN1CCCC1=O>[OH:2][C:3]1[CH:12]=[C:11]([CH3:13])[C:10]2[C:9](=[O:14])[NH:8][C@@H:7]3[CH2:15][N:16]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:17][C@H:6]3[C:5]=2[CH:4]=1

Participants

5

Reactant 3

HCID 7969ThiophenolHCID 11430Potassium CarbonateHCID 69057359HCID 69057359, compound

Product 1

HCID 69053351HCID 69053351, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
160 °C

Procedure

To a solution of (±)-trans-tert-butyl 8-methoxy-6-methyl-5-oxo-3,3a,4,5-tetrahydro-1H-pyrrolo[3,4-c]isoquinoline-2(9bH)-carboxylate from Example 72, Part C (0.43 g, 1.29 mmol) in 8 mL of N-methylpyrrolidinone was added thiophenol (0.15 mL, 1.42 mmol) and potassium carbonate (27 mg, 0.19 mmol). The resulting mixture was stirred in a sealed vial at 160° C. for 4 h. The solution was allowed to cool and was partitioned between ether and 1N NaOH. The aqueous layer was washed with ether. The combined organic layers were discarded. The aqueous layer was acidified with 12 N HCl, whereby a solid precipitated out of solution. The mixture was filtered and the solid washed with water and dried in vacuo to afford 0.26 g (65%) of the title compound as an off-white solid. LRMS (ESI): 319.3 (M+H)+.

Workup

  1. temperatureto cool
  2. customwas partitioned between ether and 1N NaOH
  3. washThe aqueous layer was washed with ether
  4. customprecipitated out of solution
  5. filtrationThe mixture was filtered
  6. washthe solid washed with water
  7. customdried in vacuo

Sources & evidence

ORD record
ord-8b361d26a6de4ed6bee483727baed07f
Source dataset
uspto-grants-2009_08
Patent number
US07572805B2

Reaction notes

Loading…