An expeditious preparation of E-2-amino-5-hydroxyadamantane and its Z-isomer

Tetrahedron Letters

Volumn 47, Issue 46, 2006, Pages 8063-8067

  Jaroskova, Libuse ^a   Van der Veken, Louis ^a   de Belser, Paul ^a   Diels, Gaston ^a   de Groot, Alex ^a   Linders, Joannes T M ^a  

^a JANSSEN RESEARCH AND DEVELOPMENT   (Belgium)

Author keywords

Adamantane; Heterogeneous catalysis; Reductive amination; Stereoisomers; Stereoselective

Indexed keywords

DIISOPROPYL ETHER; HYDROXYL GROUP; SOLVENT;

AMINATION; ARTICLE; CATALYST; CYCLIZATION; DEBENZYLATION; ISOMER; STEREOCHEMISTRY;

EID: 33749538037     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.09.056     Document Type: Article

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35. 3/MeOH using 5% Pd/C as the catalyst to give an 86% yield of a 13:1 mixture of E- and Z-4-aminoadamantane-1-carboxylic acid.
36. 4, the organic layer was evaporated to yield an oily residue, which was diluted with diisopropyl ether and set to crystallize. Crystalline 5 was filtered (26 g, 0.095 mol, 48% yield). Compound 5 (23 g, 0.084 mol) was dissolved in MeOH (250 mL), 10% Pd-C (3 g) was added and the mixture was hydrogenated during 16 h. The catalyst was filtered, and the filtrate was evaporated to give 1 (13.5 g, 95%).
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39. 4 and evaporated to give 4.5 g of 5-hydroxy-2-adamantanone 3 (27 mmol, 51%), identical to authentic material.