Hydrochloric Acid → HCID 24753518, compound

HRID 420806Notes

Reaction equation

HRID 420806 reaction equation
[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([O:17]C3CCCCO3)=[CH:14][CH:15]=2)[C:10]([C:24](=[O:26])[CH3:25])=[C:9]1[CH:27]([CH3:29])[CH3:28])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl>CO>[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([OH:17])=[CH:14][CH:15]=2)[C:10]([C:24](=[O:26])[CH3:25])=[C:9]1[CH:27]([CH3:29])[CH3:28])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 58986356HCID 58986356, compound2×

Product 1

HCID 24753518HCID 24753518, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

General Procedure D. To a solution of 1-(1-benzyl-2-isopropyl-5-(tetrahydropyran-2-yloxy)-1H-indol-3-yl)ethanone (Compound 14, 60 mg, 0.16 mmol) in MeOH was added aq. HCl (1 mL), and the solution was stirred for 5 min. at room temperature. The reaction was quenched by adding 5% aqueous NaHCO3 (2 mL), and the product was extracted with EtOAc (30 mL). The organic layer was separated, and washed with water, and brine, and dried (Na2SO4), and the solvent was removed under vacuum. Flash chromatography on silica gel with 20% EtOAc in hexane gave 1-(1-benzyl-5-hydroxy-2-isopropyl-1H-indol-3-yl)ethanone (Compound 17) as a white solid.

Workup

  1. customThe reaction was quenched
  2. additionby adding 5% aqueous NaHCO3 (2 mL)
  3. extractionthe product was extracted with EtOAc (30 mL)
  4. customThe organic layer was separated
  5. washwashed with water, and brine
  6. dry with materialdried (Na2SO4)
  7. customthe solvent was removed under vacuum

Sources & evidence

ORD record
ord-64b9afb1c90545ce8a8fb063c53f2e3a
Source dataset
uspto-grants-2012_01
Patent number
US08097644B2

Reaction notes

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