Aluminium lithium hydride → HCID 73656250, compound

HRID 1885729Notes

Reaction equation

HRID 1885729 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][N:8]1[C:12]2[CH2:13][CH2:14][C:15]3[C:16]4([CH3:27])[CH:25]([CH3:26])[CH:9]1[CH2:10][C:11]=2[C:22]=3[C:21](=O)[C:20](=O)[NH:19][CH:18]=[CH:17]4>O1CCCC1>[CH3:7][N:8]1[C:12]2[CH2:13][CH2:14][C:15]3[C:16]4([CH3:27])[CH:25]([CH3:26])[CH:9]1[CH2:10][C:11]=2[C:22]=3[CH:21]=[CH:20][NH:19][CH:18]=[CH:17]4

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 57312051HCID 57312051, compound

Product 1

HCID 73656250HCID 73656250, compoundYield 35.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred slurry of 11.35 g of lithium aluminum hydride and 700 ml of tetrahydrofuran, cooled to 0° C. under nitrogen, was added, via cannula, a solution of 8.50 g of 1,2,3,4,5,6-hexahydro-3,6,12-trimethyl-2,6-methanopyrrolo[2,3-j][3]benzazocine-10,11(9H)-dione. The reaction mixture was refluxed for 3 hours, cooled to 0° C., and quenched with 10% aqueous tetrahydrofuran. The aqueous mixture was then dried over anhydrous sodium sulfate, filtered, and concentrated. The concentrate was purified by means of flash chromatography (silica gel; 2% triethylamine/0-3% methanol/ethyl acetate) to yield 2.70 g (35%) of 1,2,3,4,5,6-hexahydro-3,6,12-trimethyl-2,6-methano-9H-pyrrolo[2,3-j][3]benzazocine.

Workup

  1. additionwas added, via cannula
  2. temperatureThe reaction mixture was refluxed for 3 hours
  3. customquenched with 10% aqueous tetrahydrofuran
  4. dry with materialThe aqueous mixture was then dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe concentrate was purified by means of flash chromatography (silica gel; 2% triethylamine/0-3% methanol/ethyl acetate)

Sources & evidence

ORD record
ord-b0ae716842b44d0cbf46f674257e510e
Source dataset
uspto-grants-1992_09
Patent number
US05145965

Reaction notes

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