Ammonia → 4-Aminotricyclo[3.3.1.1~3,7~]decane-1-carboxylic acid

HRID 1519069Notes

Reaction equation

HRID 1519069 reaction equation
O=[C:2]1[CH:9]2[CH2:10][C:5]3([C:12]([OH:14])=[O:13])[CH2:6][CH:7]([CH2:11][CH:3]1[CH2:4]3)[CH2:8]2.O.[NH3:16]>CO.[Pd]>[NH2:16][CH:2]1[CH:9]2[CH2:10][C:5]3([C:12]([OH:14])=[O:13])[CH2:6][CH:7]([CH2:11][CH:3]1[CH2:4]3)[CH2:8]2

Participants

6

Reactant 3

HCID 222AmmoniaHCID 962WaterHCID 28425154-Oxoadamantane-1-carboxylic acid

Product 1

HCID 210997894-Aminotricyclo[3.3.1.1~3,7~]decane-1-carboxylic acidYield 81%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

In a 250-mL flask, 4-oxo-adamantane-1-carboxylic acid (10 g, 51.5 mmol) was dissolved in 7N NH3 in MeOH (50 ml), and the resultant solution was added with 10% Pd/C (1 g, 10%), followed by stirring under hydrogen gas for 12 hours. After the reaction was completed, the resultant product was added with H2O and filtered to obtain 4-amino-adamantane-1-carboxylic acid (8.17 g, 81%).

Workup

  1. filtrationfiltered

Sources & evidence

ORD record
ord-e400931ba71d4a958b2e150911444f8a
Source dataset
uspto-grants-2015_07
Patent number
US09073830B2

Reaction notes

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