Trifluoroacetic anhydride → Lilolidine

Participants

Reaction Conditions

Reaction Steps

A solution of 5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinoline (4.0 g, 25.5 mmol) in methanol (100 ml) was treated with sodium cyanoborohydride (1.5 g, 23.9 mmol) then cooled to 0° C. Trifluoroacetic anhydride (15 ml) was added dropwise over 15 minutes, then the reaction was allowed to warm to room temperature and stirred for a further 2 hours. The reaction was basified with 5M aqueous potassium hydroxide then diluted with water (500 ml). The mixture was extracted with dichloromethane (3×100 ml) and the combined organic extracts were dried with anhydrous sodium sulfate and evaporated to dryness to obtain 1,2,5,6-tetrahydro-4H-pyrrolo[3,2,1-ij]quinoline as a colorless oil (4.0 g) which was used without further purification. LCMS: 160 [M+H].

Provenance & Evidence