Water → HCID 86755476, compound

HRID 1421897Notes

Reaction equation

HRID 1421897 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([N:14]1[C@@H:22]2[C@@H:17]([CH2:18][C:19]3[CH:26]=[CH:25][CH:24]=[CH:23][C:20]=3[CH2:21]2)[CH2:16][C:15]1=O)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.O.[OH-].[Na+]>O1CCCC1>[CH2:7]([N:14]1[C@@H:22]2[C@@H:17]([CH2:18][C:19]3[CH:26]=[CH:25][CH:24]=[CH:23][C:20]=3[CH2:21]2)[CH2:16][CH2:15]1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 86755475HCID 86755475, compound

Product 1

HCID 86755476HCID 86755476, compoundYield 75.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred suspension of lithium aluminium hydride (0.96 g, 25 mmol) in dry tetrahydrofuran (30 ml) at 0° C. under argon, was added cis-1-benzyl-1,3,3a,4,9,9a-hexahydro-2H-benz[f]indol-2-one (1.75 g, 6 mmol) in dry tetrahydrofuran (5 ml). The resultant mixture was then heated at reflux for 6 h, cooled to 0° C. and, with vigorous stirring, water (1 ml) was added, followed by aqueous 10% sodium hydroxide (5 ml) and water (2 ml). The resultant mixture was filtered and the solid residue was washed with dichloromethane (10 ml). The filtrate was dried (Na2SO4) and the solvent evaporated in vacuo to give the title compound as a yellow oil (1.2 g, 72%).

Workup

  1. temperatureat reflux for 6 h
  2. additionwas added
  3. filtrationThe resultant mixture was filtered
  4. washthe solid residue was washed with dichloromethane (10 ml)
  5. dry with materialThe filtrate was dried (Na2SO4)
  6. customthe solvent evaporated in vacuo

Sources & evidence

ORD record
ord-aae8a2c5e88c44e79c9113b973171d77
Source dataset
uspto-grants-2000_06
Patent number
US06080752

Reaction notes

Loading…