Octahydroindolizin-7-one → Octahydroindolizin-7-amine

HRID 9872

Reaction equation

HRID 9872 reaction equation
[CH2:1]1[CH:9]2[N:4]([CH2:5][CH2:6][C:7](=O)[CH2:8]2)[CH2:3][CH2:2]1.[NH3:11].C(O)C.[H][H]>[Pd]>[NH2:11][CH:7]1[CH2:8][CH:9]2[N:4]([CH2:3][CH2:2][CH2:1]2)[CH2:5][CH2:6]1

Participants

5

Reactant 3

HCID 11240524Octahydroindolizin-7-oneHCID 22020343Ethanol, reaction products with ammonia, distn. residuesHCID 178418361HCID 178418361, compound

Product 1

HCID 21988494Octahydroindolizin-7-amineYield 98%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

(±)-1,2,3,5,6,7,8,8a-octahydroindolizin-7-one (5.0 g, 35.9 mmol) was dissolved in a solution of 2M ammonia/ethanol (54 ml, 108 mmol calculated in terms of ammonia). The resulting solution was stirred at room temperature in an atmosphere of hydrogen in the presence of 10% palladium on charcoal (500 mg) for 4 hours. At the end of this time, the reaction mixture was filtered to remove the catalyst and the filtrate was concentrated by evaporation under reduced pressure, to give the title compound (4.91 g) as a colorless oil (yield 98%).

Workup

  1. filtrationAt the end of this time, the reaction mixture was filtered
  2. customto remove the catalyst
  3. concentrationthe filtrate was concentrated by evaporation under reduced pressure

Sources & evidence

ORD record
ord-d4445a4fa7c3408b8f17654f35a6a381
Source dataset
uspto-grants-2006_08
Patent number
US07091352B2

Linked notes

Loading…