Aluminium lithium hydride → HCID 22463936, compound

HRID 1935327Notes

Reaction equation

HRID 1935327 reaction equation
SCCCS[C:6](=[O:28])[CH2:7][C:8]1([CH2:23][CH2:24][N:25]([CH3:27])[CH3:26])[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[CH2:12][CH2:11][C:10]2[CH:19]=[CH:20][CH:21]=[CH:22][C:9]1=2.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1.C(OCC)(=O)C>[CH3:27][N:25]([CH3:26])[CH2:24][CH2:23][C:8]1([CH2:7][CH2:6][OH:28])[C:9]2[CH:22]=[CH:21][CH:20]=[CH:19][C:10]=2[CH2:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]1=2

Participants

5

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 22464015HCID 22464015, compound

Product 1

HCID 22463936HCID 22463936, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of [5-(2-dimethylaminoethyl)-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-yl]-thioacetic acid-S-(3 mercapto-propyl)ester (104), 3.1 g, 7.5 mmol) in 50 mL of THF, maintained under an argon atmosphere, was added lithium aluminum hydride (37.5 mL of a 1M solution in THF; 37.5 mmol) dropwise. The clear solution was refluxed for 5 hours and then cooled to 0° C. The mixture was diluted with ethyl acetate and quenched with 10% sodium hydroxide. The resulting slurry was filtered over celite and the organic layer was washed with saturated aqueous sodium bicarbonate and brine, dried the over sodium sulfate, filtered, and evaporated to dryness. The resulting oil was purified by chromatography on silica gel (95:5:0.5 of methylene chloride:methanol:ammonium hydroxide). The product fractions were evaporated to dryness to yield the title product. as an oil.

Workup

  1. temperatureThe clear solution was refluxed for 5 hours
  2. customquenched with 10% sodium hydroxide
  3. filtrationThe resulting slurry was filtered over celite
  4. washthe organic layer was washed with saturated aqueous sodium bicarbonate and brine
  5. dry with materialdried the over sodium sulfate
  6. filtrationfiltered
  7. customevaporated to dryness
  8. customThe resulting oil was purified by chromatography on silica gel (95:5:0.5 of methylene chloride:methanol:ammonium hydroxide)
  9. customThe product fractions were evaporated to dryness

Sources & evidence

ORD record
ord-04fd56dfa7474be0bf3f490f20c1f06c
Source dataset
uspto-grants-2002_05
Patent number
US06387893B1

Reaction notes

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