HCID 67386825, compound → HCID 67387029, compound

HRID 2408832Notes

Reaction equation

HRID 2408832 reaction equation
[CH2:1]([N:8]1[CH2:25][CH2:24][C:11]2([C:14](=[O:15])[N:13](OCC3C=CC=CC=3)[CH2:12]2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>CO.[Ni]>[CH2:1]([N:8]1[CH2:9][CH2:10][C:11]2([C:14](=[O:15])[NH:13][CH2:12]2)[CH2:24][CH2:25]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 67386825HCID 67386825, compound

Product 1

HCID 67387029HCID 67387029, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

A 2-L pressure bottle, equipped with a thermocouple and H2 inlet/outlet, was charged with Raney®-nickel (7.0 g). The Raney®-nickel was washed with methanol (3×, slurry and decant supernatant) and a solution of 7-benzyl-2-benzyloxy-2,7-diaza-spiro[3.5]nonan-1-one from Example 7C (28.3 g, 0.084 mol) in methanol (280 mL) was added. The reaction was placed on a Parr shaker and agitated overnight at 50° C. under an atmosphere of H2 (40 psi). The catalyst was removed by filtration and rinsed with methanol. The solution of product with benzyl alcohol was concentrated in vacuo. The benzyl alcohol was removed by azeotropic distillation, twice adding water (250 mL) and concentrating in vacuo. 2-Propanol was used to chase the water, twice adding 2-propanol (250 mL) and concentrating in vacuo to an oil. Heptane (500 mL) was added and the product was allowed to crystallize. After concentrating in vacuo to a final volume of 100 mL, the product was collected by filtration and washed with heptane (25 mL). Drying in a vacuum oven at 40° C. under a flow of N2 afforded the titled compound as a solid. 1H NMR (400 MHz, CDCl3) δ ppm 1.75-1.84 (m, 2H) 1.98-2.08 (m, 2 H) 2.19-2.31 (m, 2 H) 2.71-2.83 (m, 2 H) 3.13 (s, 2 H) 3.50 (s, 2 H) 5.69 (s, 1 H) 7.21-7.38 (m, 5 H).

Workup

  1. washThe Raney®-nickel was washed with methanol (3×, slurry and decant supernatant)
  2. customThe catalyst was removed by filtration
  3. washrinsed with methanol
  4. concentrationThe solution of product with benzyl alcohol was concentrated in vacuo
  5. customThe benzyl alcohol was removed by azeotropic distillation, twice adding water (250 mL)
  6. concentrationconcentrating in vacuo
  7. concentrationconcentrating in vacuo to an oil
  8. additionHeptane (500 mL) was added
  9. customto crystallize
  10. concentrationAfter concentrating in vacuo to a final volume of 100 mL
  11. filtrationthe product was collected by filtration
  12. washwashed with heptane (25 mL)
  13. dry with materialDrying in a vacuum oven at 40° C. under a flow of N2

Sources & evidence

ORD record
ord-800fd72fa0c1430d98f9bf32fec43297
Source dataset
uspto-grants-2014_08
Patent number
US08815869B2

Reaction notes

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