Glycine → HCID 1631538, compound

HRID 849435Notes

Reaction equation

HRID 849435 reaction equation
[NH2:1][CH2:2][C:3]([OH:5])=[O:4].[CH:6]12[CH2:15][CH:10]3[CH2:11][CH:12]([CH2:14][CH:8]([CH2:9]3)[C:7]1=O)[CH2:13]2.[H][H]>[Pd].C(O)(=O)C>[CH:6]12[CH2:15][CH:10]3[CH2:11][CH:12]([CH2:14][CH:8]([CH2:9]3)[CH:7]1[NH:1][CH2:2][C:3]([OH:5])=[O:4])[CH2:13]2

Participants

6

Reactant 3

HCID 750GlycineHCID 64151AdamantanoneHCID 178418361HCID 178418361, compound2×

Product 1

HCID 1631538HCID 1631538, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

A 600 ml stainless steel Parr reactor, equipped with a stirrer, two inlets, one with a tubing reaching nearly to the bottom of the reactor, and an outlet was used. Into the open reactor there were charged 100 grams of glycine (Aldrich, 99+%), 206.7 grams of 2-adamantanone (Aldrich, 99%), 10 grams of palladium (5%) on charcoal, and 300 grams of glacial acetic acid. The reactor was closed and dry nitrogen was passed through said one inlet into the reaction mixture to replace the air in the reaction mixture and in the reactor. The nitrogen was turned off and the reactor was pressurized with hydrogen through the other inlet. Under a hydrogen pressure of 725 psig (5100 kPa), the reaction mixture was heated to 100° C. and stirred at this temperature for 5 days. After cooling down to room temperature, the excess hydrogen was vented from the reactor and the reactor was opened. The mixture was filtered by suction to remove the solid Pd/C catalyst. The filtrate was evaporated to remove the acetic acid and water. The crude product was washed with ether and recrystallized from a dilute aqueous solution. A pure product was obtained after two recrystallization. Elemental analysis:Calculated for C12H1 7NO2 :C:68.67; H:9.15; N:6.69. Found C:68.85; H:9.12; N:6.75. M.P.:255.4 C (by DSC at 10 C/min. under He).

Workup

  1. customThe reactor was closed
  2. temperatureAfter cooling down to room temperature
  3. filtrationThe mixture was filtered by suction
  4. customto remove the solid Pd/C catalyst
  5. customThe filtrate was evaporated
  6. customto remove the acetic acid and water
  7. washThe crude product was washed with ether
  8. customrecrystallized from a dilute aqueous solution
  9. customA pure product was obtained
  10. customafter two recrystallization

Sources & evidence

ORD record
ord-aab3e34f6f0b46fc9855906abd1a9778
Source dataset
uspto-grants-2000_01
Patent number
US06013239

Reaction notes

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