Aluminum dichloride → HCID 14330437, compound

Participants

Reaction Conditions

Reaction Steps

Into a round bottom flask was placed 5 g (0.04 moles) hexahydro-3H-pyrrolizin-3-one, described in CA, 86 89512 (1977) in 100 mL of dry THF. This was cooled to -40° C. and 20 mL of 2.0M phenyllithium in cyclohexane/ether was added over 40 min keeping the temperature below -20° C. The reaction mixture was stirred at -20° C. for 40 min and added to a suspension of AlCl2H made by adding 5.34 g (0.04 moles) aluminum chloride in 25 mL of dry ether to a suspension of 1.52 g (0.04 moles) LAH in ether. The reaction mixture was stirred overnight under nitrogen. To the reaction mixture was added 120 mL of water and it was stirred for one hr. The solid was filtered off and washed well with ether. The filtrate was made basic with 3N sodium hydroxide and extracted several times with ether. The ether layers were combined, washed with brine and dried (K2CO3). The solvent was removed in vacuo. The residue was taken up in ether, washed with water and extracted with 3N hydrogen chloride. The acidic layer was made basic by sodium hydroxide addition and extracted with ether. The ether layer was washed with brine, dried (K2CO3) and the solvent evaporated in vacuo. The resulting oil was flashed chromatographed on silica gel using 1:7 acetone:hexane as the eluant. The resulting oil was treated with one equivalent of fumaric acid in 2-propanol to give the salt which was recrystallized from 2-propanol to give 680 mg of hexahydro-3-phenyl-1H-pyrrolizine (E)-2-butenedioate (9%), mp 143°-145.5° C.

Provenance & Evidence