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Process for preparation of Adamantane-1-methanol

IP.com Disclosure Number: IPCOM000237805D
Publication Date: 2014-Jul-14
Document File: 1 page(s) / 11K

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Process for preparation of Adamantane-1-methanol

    Adamantane-1-methanol can be prepared by reduction ofAdamantane-1- carboxylic acid using a VITRIDE ® solution .

    The obtained Adamantane-1-methanol can be used to prepare(1S,3S,5S)- 2-[(2S)-2-amino-2-(3-hydroxy-1-adamantyl) acetyl]-2-azabicyclo[3.1.0]hexane-3- carbonitrile.

Procedure:

    100 gm Adamantane -1-carboxilic acid (referred to as Compound-1) was dissolved in 1000 ml tetrahedronfuran at room temperature under nitrogen atmosphere. The obtained solution and vitride solution (440 ml,65% in toluene) diluted in 400 ml toluene was slowly added over a period of 45-60 minutes at temperature of from about -5ºC to about 5ºC. After completion of the addition the temperature was raised to 20ºC and the mixture was stirred to get completion of reaction (approximately 4-5 hours). After completion of the reaction, the reaction mass was quenched by adding 1000 ml of 10% sulphuric acid at at temperature of from about -5ºC to about 5ºC. The temperature was raised to 30ºC and the mixture was stirred for 2 to 2.5 hours and both the layers were separated. The Aqueous layers were extracted with 300 ml of toluene and total organic layer was combined and washed with 5%,1000 ml sodium bicarbonate solution. The organic layer was distilled under vacuum at below 50 ºC and the product was crystallized from heptanes. Yield 92%, purity GC- 99.5%