D-Psicose → 4-Aminoadamantan-1-ol

HRID 1990990Notes

Reaction equation

HRID 1990990 reaction equation
[OH:1][C:2]12[CH2:11][CH:6]3[CH2:7][CH:8]([CH2:10][CH:4]([C:5]3=[N:12]O)[CH2:3]1)[CH2:9]2.OCC1(OC[C@@H](O)[C@@H](O)[C@H]1O)O.[H][H]>CCO.[Pd]>[NH2:12][CH:5]1[CH:6]2[CH2:11][C:2]3([OH:1])[CH2:9][CH:8]([CH2:10][CH:4]1[CH2:3]3)[CH2:7]2

Participants

6

Reactant 3

HCID 441036D-PsicoseHCID 230089835-Hydroxy-adamantan-2-one oximeHCID 178418361HCID 178418361, compound

Product 1

HCID 28574474-Aminoadamantan-1-olYield 89.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Pd/C (5%, 0.05 g) was added to a mixture of 5-hydroxy-adamantan-2-one oxime (1 g, 5.5 mmol) in EtOH in a Parr hydrogenation bottle. The hydrogenation reaction was performed in a Parr hydrogenation instrument with 55 Psi pressure of hydrogen at room temperature for 72 hours. The mixture was filtered through celite and concentrated under vacuum to dryness to give 4-amino-adamantan-1-ol (0.82 g, 89%).

Workup

  1. customThe hydrogenation reaction
  2. filtrationThe mixture was filtered through celite
  3. concentrationconcentrated under vacuum to dryness

Sources & evidence

ORD record
ord-930b8ef958234ed3a2a9568452701226
Source dataset
uspto-grants-2010_01
Patent number
US07645773B2

Reaction notes

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