Ammonium Chloride → HCID 131718506, compound

HRID 1109163Notes

Reaction equation

HRID 1109163 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH:7]1([N:12]2[C@@H:20]3[C@@H:15]([C:16]4[CH:24]=[CH:23][CH:22]=[C:21]([O:25][CH3:26])[C:17]=4[CH2:18][CH2:19]3)[CH2:14][C:13]2=O)[CH2:11][CH2:10][CH2:9][CH2:8]1.[NH4+].[Cl-]>C1COCC1>[CH:7]1([N:12]2[C@@H:20]3[C@@H:15]([C:16]4[CH:24]=[CH:23][CH:22]=[C:21]([O:25][CH3:26])[C:17]=4[CH2:18][CH2:19]3)[CH2:14][CH2:13]2)[CH2:11][CH2:10][CH2:9][CH2:8]1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 21226445Aluminium lithium hydrideHCID 131718505HCID 131718505, compound

Product 1

HCID 131718506HCID 131718506, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

0.53 g (0.014 mol) of lithium aluminum hydride was suspended in 25 ml of THF under argon. A solution of 2.0 g (0.007 mol) of rac-cis-3-cyclopentyl-1,3,3a,4,5,9b-hexahydro-6-methoxy-2H-benzo[e]indol-2-one in 50 ml of THF was added dropwise thereto and the mixture was boiled under reflux for 1 hour. 10 ml of a saturated aqueous NH4Cl solution was cautiously added dropwise thereto and the mixture was filtered. The filtrate was extracted with ethyl acetate, the organic phase was washed with water, dried with MgSO4, filtered and the filtrate was concentrated. There were obtained 1.8 g (95%) of oily rac-cis-3-cyclopentyl-2,3,3a,4,5,9b-hexahydro-6-methoxy-1H-benzo[e]indole.

Workup

  1. temperatureunder reflux for 1 hour
  2. filtrationthe mixture was filtered
  3. extractionThe filtrate was extracted with ethyl acetate
  4. washthe organic phase was washed with water
  5. dry with materialdried with MgSO4
  6. filtrationfiltered
  7. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-52cf91af9a924653b5336086f2108bd4
Source dataset
uspto-grants-1994_06
Patent number
US05318966

Reaction notes

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