HCID 20353247, compound → HCID 20353266, compound

HRID 372101Notes

Reaction equation

HRID 372101 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[C:7]([C:10]1[CH:11]=[CH:12][C:13]2[CH:28]3[CH2:29][C:15]4([CH2:19][N:18]([CH2:20][CH:21]5[CH2:25][CH2:24][CH2:23][CH2:22]5)[CH2:17][CH:16]4[C:26]4[CH:33]=[CH:32][CH:31]=[CH:30][C:27]=43)[C:14]=2[CH:34]=1)(=[O:9])[CH3:8]>CCOCC>[OH:9][CH:7]([C:10]1[CH:11]=[CH:12][C:13]2[CH:28]3[CH2:29][C:15]4([CH2:19][N:18]([CH2:20][CH:21]5[CH2:25][CH2:24][CH2:23][CH2:22]5)[CH2:17][CH:16]4[C:26]4[CH:33]=[CH:32][CH:31]=[CH:30][C:27]=43)[C:14]=2[CH:34]=1)[CH3:8]

Participants

4

Reactant 2

HCID 20353247HCID 20353247, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 20353266HCID 20353266, compoundYield 60.5%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a suspension of 0.5 g of lithium aluminum hydride in 25 ml of ether was added dropwise a solution of 2.3 g of 5-acetyl-2-cyclopentylmethyl-2,3,8,12b-tetrahydro-1H-3a,8-methanodibenzo[3,4:6,7]cyclohepta[1,2-c]-pyrrole in 10 ml of ether. The reaction mixture was heated at reflux overnight and then excess lithium aluminum hydride was destroyed by the dropwise addition of a saturated aqueous sodium sulfate solution. The suspension was filtered with the aid of diatomaceous earth, and the filtrate was evaporated to dryness. The residue was dissolved in methylene chloride, and the solution was washed with water, dried over potassium carbonate and concentrated in vacuo to give 1.4 g of 5-(α-hydroxyethyl)-2-cyclopentylmethyl-2,3,8,12b-tetrahydro-1H-3a,8-methanodibenzo[3,4:6,7]cyclohepta[1,2-c]pyrrole as an oil; nmr spectrum; δ 1.0-4.0 (m, 19); 1.3 (d, 3); 3.0-4.0 (m, 1); 4.7 (t, 1); 6.8-7.4 (m, 7).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux overnight
  3. customexcess lithium aluminum hydride was destroyed by the dropwise addition of a saturated aqueous sodium sulfate solution
  4. filtrationThe suspension was filtered with the aid of diatomaceous earth
  5. customthe filtrate was evaporated to dryness
  6. dissolutionThe residue was dissolved in methylene chloride
  7. washthe solution was washed with water
  8. dry with materialdried over potassium carbonate
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f4830b61e13a43f1879d0a7347783fca
Source dataset
uspto-grants-1978_05
Patent number
US04088772

Reaction notes

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