Water → cis-2-(3,4-Dichlorophenethyl)-3a,4,7,7a-tetrahydroisoindoline

HRID 1586777Notes

Reaction equation

HRID 1586777 reaction equation
[H-].COCCO[Al+]OCCOC.[Na+].[H-].[OH-].[Na+].O.[Cl:18][C:19]1[CH:20]=[C:21]([CH2:26][C:27]([N:29]2[CH2:37][C@H:36]3[C@H:31]([CH2:32][CH:33]=[CH:34][CH2:35]3)[CH2:30]2)=O)[CH:22]=[CH:23][C:24]=1[Cl:25]>C1(C)C=CC=CC=1>[Cl:18][C:19]1[CH:20]=[C:21]([CH:22]=[CH:23][C:24]=1[Cl:25])[CH2:26][CH2:27][N:29]1[CH2:37][C@H:36]2[C@H:31]([CH2:32][CH:33]=[CH:34][CH2:35]2)[CH2:30]1

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 21584525Sodium bis(2-methoxyethoxy)aluminiumhydrideHCID 70073714cis-2-(3,4-Dichlorophenylacetyl)-3a,4,7,7a-tetrahydroisoindole

Product 1

HCID 57298220cis-2-(3,4-Dichlorophenethyl)-3a,4,7,7a-tetrahydroisoindoline

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

To 0.70 g of this intermediate and 3 mL of toluene was added at 0° 2 mL of 3.4 M sodium bis(2-methoxyethoxy)aluminum hydride in toluene and the mixture was stirred in an ice bath for 1 hour and at room temperature for 4 hours. Aqueous sodium hydroxide solution (15%, 5 mL) and water (10 mL) were added with cooling. From the toluene layer there was obtained 0.66 g of crude product which was partitioned into a neutral and basic fraction. The latter was short-path distilled (140° bath temperature, 0.003 mm) to give 0.48 g of cis-2-(3,4-dichlorophenethyl)-3a,4,7,7a-tetrahydroisoindoline. 'H NMR (in CDCl3) : δ7.3 (AB quartet, 2H);7.0 (d/d, 1H); 5.8 (m, 2H); 3.0 (m, 2H); 2.8 (m, 4H), among others. The hydrochloride had m.p. 201°-202° after recrystallization from ethanol.

Workup

  1. temperaturewith cooling
  2. customwas partitioned into a neutral and basic fraction
  3. distillationThe latter was short-path distilled (140° bath temperature, 0.003 mm)

Sources & evidence

ORD record
ord-ee806673158f4d3b9287d6a6d84792ed
Source dataset
uspto-grants-1993_06
Patent number
US05216018

Reaction notes

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