Aluminium lithium hydride → HCID 53827587, compound

HRID 2226930Notes

Reaction equation

HRID 2226930 reaction equation
C([O:3][C:4]([CH:6]1[CH2:20][C:9]2[N:10]([CH3:19])[C:11]3[CH:12]=[CH:13][C:14]([O:17][CH3:18])=[CH:15][C:16]=3[C:8]=2[CH2:7]1)=O)C.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[CH3:18][O:17][C:14]1[CH:13]=[CH:12][C:11]2[N:10]([CH3:19])[C:9]3[CH2:20][CH:6]([CH2:4][OH:3])[CH2:7][C:8]=3[C:16]=2[CH:15]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 53735277HCID 53735277, compound

Product 1

HCID 53827587HCID 53827587, compoundYield 74.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1,2,3,4-tetrahydro-7-methoxy-4-methylcyclopent[b]indole-2-carboxylic acid ethyl ester (2.0 g, 0.007 mole) in 30 ml of dry tetrahydrofuran, was added lithium aluminum hydride (1M solution in tetrahydrofuran, 15 ml, 0.015 mole). After stirring at reflux for three hours, the mixture was cooled, quenched with 5 ml of saturated ammonium chloride solution and then diluted with 50 ml of ether. The mixture was filtered, and the filtrate concentrated to a yellow oil (~2 g). This oil was eluted on a silica gel column with 10% ethyl acetate/dichloromethane via HPLC. The desired fractions were combined and concentrated to give the product as a thick yellow oil (1.2g).

Workup

  1. temperatureat reflux for three hours
  2. temperaturethe mixture was cooled
  3. customquenched with 5 ml of saturated ammonium chloride solution
  4. additiondiluted with 50 ml of ether
  5. filtrationThe mixture was filtered
  6. concentrationthe filtrate concentrated to a yellow oil (~2 g)
  7. washThis oil was eluted on a silica gel column with 10% ethyl acetate/dichloromethane via HPLC
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-8528e171f2c24a5781a76dc257f7fdcd
Source dataset
uspto-grants-1994_09
Patent number
US05350762

Reaction notes

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