4-(3-Phenylpropyl)pyridine N-oxide → HCID 86686866, compound

Temperature

0 °C

To a stirring solution of 4-phenylpropylpyridine-N-oxide (278 mg, 1.31 mmol) in methylene chloride (20 mL) was added (R,R)-Jacobsen catalyst (237.0 mg, 0.3732 mmol) and a solution of sodium hypochlorite (2.0 M in water; 16 mL, 32 mmol) at 0° C. The resulting brown suspension was stirred at 0° C. for 15 minutes then a solution of 6-chloro-1H-indene (1) (2.81 g, 18.6 mmol) in methylene chloride (20 mL) was added via syringe with simultaneous addition of additional sodium hypochlorite (2.0M in water; 16 mL, 32 mmol). The reaction was stirred at 0° C. for one hour then the ice bath was removed and the reaction was stirred at room temperature for 1 hr. An aliquot was taken and TLC on silica (hexanes) showed all starting material consumed. The reaction was poured into brine and extracted with methylene chloride. The combined extracts were washed with saline, then dried over sodium sulfate, filtered, and evaporated under reduced pressure to leave crude product which solidified when placed under hi-vacuum. Yield ˜3.7 g of a brown solid. 1H NMR (400 MHz, DMSO) δ 7.55 (d, J=7.6 Hz, 1H), 7.32 (s, 1H), 7.23 (d, J=7.3 Hz, 1H), 4.36 (s, 1H), 4.16 (s, 1H), 3.03 (dd, J=45.8, 18.2 Hz, 2H).

1. customat 0° C
2. stirringThe reaction was stirred at 0° C. for one hour
3. customthe ice bath was removed
4. stirringthe reaction was stirred at room temperature for 1 hr
5. customconsumed
6. additionThe reaction was poured into brine
7. extractionextracted with methylene chloride
8. washThe combined extracts were washed with saline
9. dry with materialdried over sodium sulfate
10. filtrationfiltered
11. customevaporated under reduced pressure
12. customto leave crude product which

ORD record

ord-1186ec6c7ebf4fc6aabfcf035d4d6e19

Source dataset

uspto-grants-2014_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08809356B2