Water → HCID 12822473, compound

HRID 980293Notes

Reaction equation

HRID 980293 reaction equation
C1(CO[C:9](=O)[NH:10][CH2:11][CH2:12][C:13]2[C:21]3[C:16](=[CH:17][CH:18]=[C:19]([CH2:22][NH:23][S:24]([CH3:27])(=[O:26])=[O:25])[CH:20]=3)[NH:15][CH:14]=2)C=CC=CC=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.C(OCC)(=O)C>C1COCC1>[CH3:9][NH:10][CH2:11][CH2:12][C:13]1[C:21]2[C:16](=[CH:17][CH:18]=[C:19]([CH2:22][NH:23][S:24]([CH3:27])(=[O:25])=[O:26])[CH:20]=2)[NH:15][CH:14]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 12822511HCID 12822511, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 12822473HCID 12822473, compoundYield 107%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

A solution of phenylmethyl[2-[5-[[(methylsulphonyl)amino]methyl]-1H-indol-3-yl]ethyl]carbamate (0.02 g) in dry THF (1 ml) was added to a stirred suspension of lithium aluminium hydride (0.1 g) in THF (2 ml) and the mixture was refluxed under nitrogen for 3 h. The mixture was cooled and excess reagent was decomposed by the addition of 10% water in THF. Salt and ethyl acetate (20 ml) were added and the organic layer was dried (Na2SO4) and evaporated in vacuo to leave the title compound as a brown oil (0.015 g).

Workup

  1. temperaturethe mixture was refluxed under nitrogen for 3 h
  2. temperatureThe mixture was cooled
  3. dry with materialthe organic layer was dried (Na2SO4)
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-b5a2140a74814467a71eba57bb2970cc
Source dataset
uspto-grants-1987_01
Patent number
US04636521

Reaction notes

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