p-Toluenesulfonic acid → HCID 58986318, compound

HRID 420803Notes

Reaction equation

HRID 420803 reaction equation
[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([OH:17])=[CH:14][CH:15]=2)[C:10]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[C:9]1[CH:23]([CH3:25])[CH3:24])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[O:26]1[CH:31]=[CH:30][CH2:29][CH2:28][CH2:27]1.CC1C=CC(S(O)(=O)=O)=CC=1>C(Cl)Cl>[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([O:17][CH:27]3[CH2:28][CH2:29][CH2:30][CH2:31][O:26]3)=[CH:14][CH:15]=2)[C:10]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[C:9]1[CH:23]([CH3:24])[CH3:25])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 80803,4-dihydro-2H-pyranHCID 58986350HCID 58986350, compound2×

Product 1

HCID 58986318HCID 58986318, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a cold (0° C.) solution of 1-benzyl-5-hydroxy-2-isopropyl-1H-indole-3-carboxylic acid, ethyl ester (Compound 1, 2.3 gm, 6.82 mmol) in CH2Cl2 (31 mL) was added dihydropyran (DHP, 3.1 g, 36.9 mmol) and p-TsOH (50 mg). The cooling bath was removed, and the solution was stirred at ambient temperature for 16 h. The reaction was quenched by adding aqueous NaHCO3 (20 mL) and CH2Cl2 (50 mL). The layers were separated, and the organic layer was washed with brine (20 mL), and dried (MgSO4), and solvent removed under vacuum. The crude mixture was purified by silica gel flash chromatography by eluting with 10% EtOAc in hexanes to isolate 1-benzyl-2-isopropyl-5-(tetrahydropyran-2-yloxy)-1H-indole-3-carboxylic acid, ethyl ester (Compound 11) as a thick pale yellow oil.

Workup

  1. customThe cooling bath was removed
  2. customThe reaction was quenched
  3. additionby adding aqueous NaHCO3 (20 mL) and CH2Cl2 (50 mL)
  4. customThe layers were separated
  5. washthe organic layer was washed with brine (20 mL)
  6. dry with materialdried (MgSO4), and solvent
  7. customremoved under vacuum
  8. customThe crude mixture was purified by silica gel flash chromatography
  9. washby eluting with 10% EtOAc in hexanes

Sources & evidence

ORD record
ord-9a7742063f6947c9997647866e834b88
Source dataset
uspto-grants-2012_01
Patent number
US08097644B2

Reaction notes

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