Nitrogen → 6-Oxospiro[2.5]octane-5-carbonitrile

HRID 1852473Notes

Reaction equation

HRID 1852473 reaction equation
[O:1]=[C:2]1[CH2:9][CH2:8][C:5]2([CH2:7][CH2:6]2)[CH:4]=[C:3]1[C:10]#[N:11].N#N>CO.[Pd]>[O:1]=[C:2]1[CH2:9][CH2:8][C:5]2([CH2:6][CH2:7]2)[CH2:4][CH:3]1[C:10]#[N:11]

Participants

5

Reactant 2

HCID 947NitrogenHCID 867310096-Oxospiro[2.5]oct-4-ene-5-carbonitrile

Product 1

HCID 867310106-Oxospiro[2.5]octane-5-carbonitrile

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

6-Oxospiro[2.5]oct-4-ene-5-carbonitrile (0.16 g, 1.1 mmol) was dissolved in MeOH (11 mL) and combined with 10% palladium on activated carbon (0.12 g, 0.11 mmol). The resulting mixture was subjected to alternating vacuum and H2 gas (4×). The mixture was then stirred under an atmosphere of H2 (50 psi) for 16 hours. The mixture was then subjected to alternating vacuum and N2 gas (4×). The mixture was filtered through celite and rinsed with MeOH. The filtrate was concentrated in vacuo to afford the title compound. The material was used without further purification.

Workup

  1. filtrationThe mixture was filtered through celite
  2. washrinsed with MeOH
  3. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-0c79da19d7264276beaac0fcf37660f1
Source dataset
uspto-grants-2015_02
Patent number
US08962608B2

Reaction notes

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