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

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Reaction Steps

To 0.70 g of this intermediate and 3 mL of toluene was added at 0° 2 mL of 3.4M 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. Anal. Calcd. for C16H20C13N: C, 57.76; H, 6.06; N, 4.21. Found: C, 57.86; H, 6.04; N, 4.09.

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