HCID 12822523, compound → HCID 20222397, compound

HRID 980306Notes

Reaction equation

HRID 980306 reaction equation
[CH3:1][S:2]([NH:5][CH2:6][C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[NH:12][CH:11]=[C:10]2[C:16](=O)[C:17](OCC)=[O:18])(=[O:4])=[O:3].[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[OH:18][CH2:17][CH2:16][C:10]1[C:9]2[C:13](=[CH:14][CH:15]=[C:7]([CH2:6][NH:5][S:2]([CH3:1])(=[O:4])=[O:3])[CH:8]=2)[NH:12][CH:11]=1

Participants

4

Reactant 2

HCID 12822523HCID 12822523, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 20222397HCID 20222397, compoundYield 72.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Ethyl 5-[[(methylsulphonyl)amino]methyl]-α-oxo-1H-indole-3-acetate (0.50 g) was added portionwise under nitrogen to a stirred suspension of lithium aluminium hydride (0.59 g) in dry THF (30 ml). The mixture was heated under reflux for 6 h, then cooled in an ice bath and treated dropwise with aqueous THF (15%, 20 ml) and then with water (20 ml) and extracted with ethyl acetate (6×25 ml). The extract was washed with brine (3×25 ml) and dried (Na2SO4). Removal of the solvent gave a dark brown oil which was purified by chromtography on a silica column (Merck Kieselgel 60; 10 g) eluted with cyclohexane then ethyl acetate to give the title compound as a gum (0.3 g) which failed to crystallise

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 6 h
  3. temperaturecooled in an ice bath
  4. extractionwith water (20 ml) and extracted with ethyl acetate (6×25 ml)
  5. washThe extract was washed with brine (3×25 ml)
  6. dry with materialdried (Na2SO4)
  7. customRemoval of the solvent
  8. customgave a dark brown oil which
  9. customwas purified by chromtography on a silica column (Merck Kieselgel 60; 10 g)
  10. washeluted with cyclohexane

Sources & evidence

ORD record
ord-127391c4bb324b0291ce4974ddf4a40c
Source dataset
uspto-grants-1987_01
Patent number
US04636521

Reaction notes

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