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

Temperature

0 °C

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.

1. customthe 0° C.
2. additionwas added
3. stirringthe mixture was stirred at 0° C. for 3 h
4. customThe resulting liquid layers were separated
5. extractionthe aqueous layer was extracted 3 times with CH2Cl2
6. washThe combined organic layers were washed with brine
7. dry with materialdried over MgSO4
8. customSolvents were evaporated
9. customthe crude product was purified by silica gel chromatography (eluting with 5 to 50% ethyl acetate in heptane)
10. customThe product was recrystallized from heptane

ORD record

ord-f3b7fd6368fe41eba9c2fa959fc4b7e5

Source dataset

uspto-grants-2015_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09034897B2