Water → cis-Octahydroisoindole

HRID 2051613Notes

Reaction equation

HRID 2051613 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[C:7]1(=O)[NH:11][C:10](=O)[C@H:9]2[CH2:13][CH2:14][CH2:15][CH2:16][C@@H:8]12.O>C(OCC)C.O1CCCC1>[C@@H:8]12[CH2:7][NH:11][CH2:10][C@@H:9]1[CH2:13][CH2:14][CH2:15][CH2:16]2

Participants

6

Reactant 3

HCID 962WaterHCID 6992236cis-HexahydrophthalimideHCID 21226445Aluminium lithium hydride

Product 1

HCID 10964494cis-Octahydroisoindole

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a slurry of lithium aluminium hydride (17.1 g) in dry diethyl ether (375 ml) under a nitrogen atmosphere, cis-hexahydrophthalimide (23.0 g) in dry tetrahydrofuran (300 ml) was added over a two-hour period. The mixture was refluxed for 2.5 hours, cooled and treated very slowly with excess of water. The precipitate was filtered off and the filtrate was evaporated to yield the title compound as a viscous oil, which was used in the next step without purification.

Workup

  1. temperatureThe mixture was refluxed for 2.5 hours
  2. temperaturecooled
  3. filtrationThe precipitate was filtered off
  4. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-d5fdc02a68d7413188ac41fca4b5cb6f
Source dataset
uspto-grants-1980_01
Patent number
US04181659

Reaction notes

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