HCID 57485748, compound → HCID 57485747, compound

To a solution of a mixture of t-butyl 3-(3-pyridinyl)-6-azabicyclo[3.2.1] oct-2-ene-6-carboxylate and t-butyl 3-(3-pyridinyl)-6-azabicyclo[3.2.1] oct-3-ene-6-carboxylate (150 mg) in methanol (5 ml) was added catalytic 10% Pd/C and the mixture was subjected to hydrogenolysis (45 psi) for 48 h. The reaction was filtered through Celite and concentrated by rotary evaporation, and then the residue was taken up in dichloromethane (1 ml) and treated with trifluoroacetic acid (2 ml). After 3 h, the mixture was concentrated to dryness by rotary evaporation, partitioned between water and dichloromethane, and the organic layer discarded. The aqueous layer was made basic with sodium hydroxide and extracted with dichloromethane. After drying over sodium sulfate, the filtered solution was concentrated to dryness by rotary evaporation and the residue purified by column chromatography, using a methanol/dichloromethane gradient (0-10% methanol with 1% ammonium hydroxide) as eluent. The product fractions were pooled and concentrated to give the desired product (20 mg). It was then re-chromatographed (same conditions) to give the free base (10 mg) as a brown oil.

1. filtrationThe reaction was filtered through Celite
2. concentrationconcentrated by rotary evaporation
3. additiontreated with trifluoroacetic acid (2 ml)
4. waitAfter 3 h
5. concentrationthe mixture was concentrated to dryness by rotary evaporation
6. custompartitioned between water and dichloromethane
7. extractionextracted with dichloromethane
8. dry with materialAfter drying over sodium sulfate
9. concentrationthe filtered solution was concentrated to dryness by rotary evaporation
10. customthe residue purified by column chromatography
11. concentrationconcentrated

ORD record

ord-4fad22e61d3b4c57a7c4a7ab3e40f76d

Source dataset

uspto-grants-2008_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07402592B2