Tetrahydrofuran → HCID 21087556, compound

HRID 348529Notes

Reaction equation

HRID 348529 reaction equation
[CH2:1]1[C:6]2[NH:7][C:8]3[C:9]([C:14]([O:16]CC)=O)=[CH:10][CH2:11][CH2:12][C:13]=3[C:5]=2[CH:4]=[CH:3][NH:2]1.[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+].[CH2:27]1COC[CH2:28]1>>[CH2:27]([CH:12]1[CH2:11][CH:10]=[C:9]([CH2:14][OH:16])[C:8]2[NH:7][C:6]3[CH2:1][NH:2][CH:3]=[CH:4][C:5]=3[C:13]1=2)[CH3:28]

Participants

5

Reactant 4

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 21087566HCID 21087566, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 21087556HCID 21087556, compound

Procedure

Ethyl 1,2,5,6-tetrahydropyrido[3,4-b]indole-8-carboxylate (0.56 g, 2.16 mmol) was dissolved in dry THF (30 mL) and lithium aluminum hydride (1M in THF, 10.82 mL, 10.82 mmol) was added via syringe. The mixture was heated to reflux for one hour then cooled and NaOH (5% aqueous solution, 2.67 mL) was added. The mixture was filtered through diatomaceous earth and the solvent was removed to afford 0.5 g of title compound.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for one hour
  3. temperaturethen cooled
  4. filtrationThe mixture was filtered through diatomaceous earth
  5. customthe solvent was removed

Sources & evidence

ORD record
ord-70f6cd4b95a54455a8de7d5acf017a0a
Source dataset
uspto-grants-2007_02
Patent number
US07176322B2

Reaction notes

Loading…