反应详情

A solution was prepared from 3.4 g. of dl-2-benzyloxy-6-azido-5,6,7,8-tetrahydro-1-naphthalenecarboxamide (from Example 4) and 100 ml. of isopropanol. The solution was cooled and 0.5 g. sodium borohydride added thereto in small portions. After the addition had been completed, the reaction mixture was heated to reflux temperature under a nitrogen blanket for about 18 hours. The reaction mixture was then cooled and the cooled mixture diluted with water. The aqueous mixture was made acidic by the addition of 1N aqueous hydrochloric acid. The aqueous acidic layer was extracted with ether and the ether extract discarded. The aqueous acidic layer was made basic by the addition of 10% aqueous sodium hydroxide. The alkaline layer was extracted several times with equal volumes of a 3:1 chloroform/methanol solvent mixture. The organic extracts were combined and the combined extracts washed with saturated aqueous sodium chloride and then dried. Evaporation of the solvent therefrom yielded a residue comprising dl-2-benzyloxy-6-amino-5,6,7,8-tetrahydro-1-naphthalenecarboxamide. TLC indicated a single spot at the origin. An infrared spectrum of the solid indicated no absorption attributable to an azide group. The residue was dissolved in chloroform and the chloroform solution saturated with gaseous hydrogen chloride. The solvent was removed in vacuo and the residue dissolved in methanol. Ether was added to the point of incipient precipitation and the solution was cooled overnight. Forty-eight hundredths grams of tan crystals melting above 235° C. consisting of dl-2-benzyloxy-6-amino-5,6,7,8-tetrahydro-1-naphthalenecarboxamide hydrochloride were recovered.

1. customA solution was prepared from 3.4 g
2. temperatureThe solution was cooled
3. additionAfter the addition
4. temperaturethe reaction mixture was heated
5. temperatureto reflux temperature under a nitrogen blanket for about 18 hours
6. temperatureThe reaction mixture was then cooled
7. extractionThe aqueous acidic layer was extracted with ether
8. extractionthe ether extract
9. additionThe aqueous acidic layer was made basic by the addition of 10% aqueous sodium hydroxide
10. extractionThe alkaline layer was extracted several times with equal volumes of a 3:1 chloroform/methanol solvent mixture
11. washthe combined extracts washed with saturated aqueous sodium chloride
12. customdried
13. customEvaporation of the solvent