4-(3-Phenylpropyl)pyridine N-oxide → 4-Bromo-6,6a-dihydro-1aH-indeno[1,2-b]oxirene

Temperature

0 °C

To a solution of 4-(3-phenylpropyl)pyridine N-oxide (68.88 mg, 0.323 mmol) in methylene chloride (6.00 mL) was added (S,S)-(+)-N,N′-bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexanediamino-manganese(III) chloride (58.62 mg, 0.09.23 mmol) and 2.0 M of sodium hypochlorite in water (4.00 mL) at 0° C. The resulting brown suspension was stirred at 0° C. for 15 min. To the cooled suspension was added a solution of 6-bromo-1H-indene (900 mg, 4.6141 mmol) in methylene chloride (6.00 mL) at 0° C. with simultaneous addition of 2.0 M of sodium hypochlorite in water (4.00 mL) at 0° C. The reaction was kept at 0° C. for 1 h. The reaction was allowed to warm up to room temperature and then stirred at room temperature overnight. The reaction mixture was poured into brine and then extracted with methylene chloride (4×40 mL). The combined extracts were dried over anhydrous Na2SO4, filtered and evaporated under reduced pressure. The crude product was used directly for the next reaction. The ratio of the two diastereomers was 8/1.

1. waitThe reaction was kept at 0° C. for 1 h
2. temperatureto warm up to room temperature
3. stirringstirred at room temperature overnight
4. extractionextracted with methylene chloride (4×40 mL)
5. dry with materialThe combined extracts were dried over anhydrous Na2SO4
6. filtrationfiltered
7. customevaporated under reduced pressure
8. customThe crude product was used directly for the next reaction

ORD record

ord-ea2305eae09b40db820518a486a16887

Source dataset

uspto-grants-2012_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08268826B2