Tricyclo(3.3.1.1'3,7)dec-1-ylmethanol → 1-Adamantanecarboxaldehyde

HRID 1875850Notes

Reaction equation

HRID 1875850 reaction equation
C1C=C[NH+]=CC=1.[O-][Cr](Cl)(=O)=O.[C:12]12([CH2:22][OH:23])[CH2:21][CH:16]3[CH2:17][CH:18]([CH2:20][CH:14]([CH2:15]3)[CH2:13]1)[CH2:19]2>>[C:12]12([CH:22]=[O:23])[CH2:19][CH:18]3[CH2:17][CH:16]([CH2:15][CH:14]([CH2:20]3)[CH2:13]1)[CH2:21]2

Participants

3

Reactant 2

HCID 64556Tricyclo(3.3.1.1'3,7)dec-1-ylmethanolHCID 178418287HCID 178418287, compound

Product 1

HCID 110410501-AdamantanecarboxaldehydeYield 89%

Procedure

The PCC-based oxidation of 1-adamantanemethanol will furnish 1-adamantanecarboxaldehyde in an 89% yield, as described in the literature [20]. The Schiff base condensation between 1-adamantanecarboxaldehyde and DFOB will yield the imine-based adamantane-DFOB conjugate which will be reduced by sodium cyanoborohydride (NaCNBH3) to give the secondary amine-based adamantane-DFOB conjugate. Sodium cyanoborohydride does not reduce the hydroxamate groups of DFOB to amides [21].

Sources & evidence

ORD record
ord-06495e6f75d7464daef0145c44daea5d
Source dataset
uspto-grants-2012_11
Patent number
US08309583B2

Reaction notes

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