4-(3-Phenylpropyl)pyridine N-oxide → HCID 89444796, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 9 g (42.3 mmol) of 7-Bromo-5-fluoro-1H-indene (5a) in CH2Cl2 at 0° C. was added (S,S)-(+)-N,N′-bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexanediaminomanganese(III)-chloride (Jacobsen catalyst; 1.2 g, 1.7 mmol) and 4-(3-phenylpropyl)pyridine N-oxide (1.8 g, 8.5 mmol). After stirring for 15 min at 0° C., the 0° C. cold buffered sodium hypochlorite solution was added and the mixture was stirred at 0° C. for 3 h. The resulting liquid layers were separated and the aqueous layer was extracted 3 times with CH2Cl2. The combined organic layers were washed with brine and dried over MgSO4. Solvents were evaporated and the crude product was purified by silica gel chromatography (eluting with 5 to 50% ethyl acetate in heptane). The product was recrystallized from heptane to give 3.2 g of (1aS,6aR)-5-Bromo-3-fluoro-6,6a-dihydro-1aH-1-oxa-cyclopropa[a]indene (6a) as white needles.

Provenance & Evidence