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

HRID 2389907Notes

Reaction equation

HRID 2389907 reaction equation
[OH:1][C:2]1([CH2:17][C:18]#[N:19])[C:6]2=[C:7]3[CH2:13][CH2:12][O:11][C:8]3=[N:9][CH:10]=[C:5]2[CH2:4][CH:3]1[CH:14]([CH3:16])[CH3:15].N.C(O)C>C(O)C.[Co]>[NH2:19][CH2:18][CH2:17][C:2]1([OH:1])[C:6]2=[C:7]3[CH2:13][CH2:12][O:11][C:8]3=[N:9][CH:10]=[C:5]2[CH2:4][CH:3]1[CH:14]([CH3:15])[CH3:16]

Participants

5

Reactant 2

HCID 22020343Ethanol, reaction products with ammonia, distn. residuesHCID 59179402(8-hydroxy-7-isopropyl-1,6,7,8-tetrahydro-2H-cyclopenta[d]furo[2,3-b]pyridin-8-yl)acetonitrile

Product 1

HCID 591793768-(2-aminoethyl)-7-isopropyl-1,6,7,8-tetrahydro-2H-cyclopenta[d]furo[2,3-b]pyridin-8-olYield 100%

Reagents, catalysts & solvents 2

HCID 104730CobaltCatalystHCID 702EthanolSolvent

Procedure

To a solution of (8-hydroxy-7-isopropyl-1,6,7,8-tetrahydro-2H-cyclopenta[d]furo[2,3-b]pyridin-8-yl)acetonitrile (440 mg, 1.70 mmol) in ethanol (12 mL) were added Raney cobalt (4 g) and 2M ammonia/ethanol solution (6 mL), and the mixture was stirred at room temperature for 4 hr under a hydrogen atmosphere. The catalyst was filtered through celite, and the filtrate was concentrated under reduced pressure to give the title compound (446 mg, yield 100%).

Workup

  1. filtrationThe catalyst was filtered through celite
  2. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-c55541f6b6d343e59128bec0aaa2e07d
Source dataset
uspto-grants-2012_09
Patent number
US08273761B2

Reaction notes

Loading…