4-Toluenesulfonyl chloride → 5-benzylhexahydro-1H-furo[3,4-c]pyrrole

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Reaction Steps

Using another route as shown in the accompanying schematic, one mole of the mixture of the cis-trans 3,4-bis (hydroxymethyl)tetrahydrofuran (III) can be reacted with p-toluenesulfonyl chloride according to the process of Example 9 to form a cis-trans mixture of 3,4-bis(tosyloxymethyl)tetrahydrofuran (XIX). This product, (XIX), can in turn be reacted with benzylamine according to the process of Example 10 to form 5-benzyl hexahydro-1H-furo(3,4-c)pyrrole (IX) from the cis 3,4-bis(tosyloxymethyl)tetrahydrofuran. 5-Benzyl hexahydro-1H-furo( 3,4-c)pyrrole (IX) is separated from the reaction product mixture by distillation at about 95° to 105°C. at 0.15 mm Hg. This product in turn can be debenzylated according to the method of Example 11 to form hexahydro-1H-furo(3,4-c)pyrrole.

Provenance & Evidence