Ethanol, reaction products with ammonia, distn. residues → 2-(1,6,7,8-tetrahydro-2H-cyclopenta[d]furo[2,3-b]pyridin-8-yl)ethanamine

To a solution of 1,2,6,7-tetrahydro-8H-cyclopenta[d]furo[2,3-b]pyridin-8-ylideneacetonitrile (500 mg, 2.52 mmol) in ethanol (16 mL) were added Raney cobalt (1 g) and 2M ammonia/ethanol solution (8 mL), and the mixture was stirred at room temperature for 30 hr under a hydrogen atmosphere. The catalyst was filtered through celite, and the filtrate was concentrated under reduced pressure. The residue was dissolved in methanol (20 mL), palladium-carbon powder (100 mg) was added, and the mixture was stirred at room temperature for 12 hr under a hydrogen atmosphere. The catalyst was filtered off, and the filtrate was concentrated under reduced pressure to give the title compound. The obtained title compound was used for the reaction in Examples 25, 26, 27 and 28 without purification.

1. filtrationThe catalyst was filtered through celite
2. concentrationthe filtrate was concentrated under reduced pressure
3. dissolutionThe residue was dissolved in methanol (20 mL)
4. additionpalladium-carbon powder (100 mg) was added
5. stirringthe mixture was stirred at room temperature for 12 hr under a hydrogen atmosphere
6. filtrationThe catalyst was filtered off
7. concentrationthe filtrate was concentrated under reduced pressure

ORD record

ord-98e3088264df4f27854ffb5b0ec7fe55

Source dataset

uspto-grants-2012_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08273761B2