Glycine → HCID 1631538, compound

HRID 1899750Notes

Reaction equation

HRID 1899750 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, compound

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 assembled in the hood with nitrogen and hydrogen sources. The reaction mixture was bubbled with dry nitrogen, to replace the air in the reaction mixture and in the reactor, through the inlet with a tubing reaching nearly to the bottom of 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, the reaction mixture was heated to 100° C. and stirred at this temperature for 5 days. Hydrogen was refilled whenever it was necessary. 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 rotavapped 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 C12H17NO2 : C:68.67; H:9.15; N:6.69. FoundL 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. customThe reaction mixture was bubbled with dry nitrogen
  3. additionHydrogen was refilled whenever it
  4. temperatureAfter cooling down to room temperature
  5. filtrationThe mixture was filtered by suction
  6. customto remove the solid Pd/C catalyst
  7. customto remove the acetic acid and water
  8. washThe crude product was washed with ether
  9. customrecrystallized from a dilute aqueous solution
  10. customA pure product was obtained
  11. customafter two recrystallization

Sources & evidence

ORD record
ord-9bc23d7b4d964901b60e855c09c21fea
Source dataset
uspto-grants-1996_11
Patent number
US05573746

Reaction notes

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