반응 #1806802

반응 방정식

13-amino-6,7,8,9,10,11-hexahydro-3-hydroxy-5-methyl-5,11-methanobenzocyclodecen-12(5H)-one hydrochloride dihydrate

lithium aluminum hydride

LAH

water

→

title compound

수율 68.0%

13-Amino-5,6,7,8,9,10,11,12-octahydro-5-methyl-5,11-methanobenzocyclodecen-3,12-diol

수율 68.0%

용매

THF

tetrahydrofuran

반응 조건

후처리

1. 1
   온도The reaction mixture was refluxed for 25 hours
2. 2
   온도cooled
3. 3
   여과The reaction mixture was filtered
4. 4
   세척the filtrate washed with aqueous ammonium chloride
5. 5
   건조dried (anhydrous Na2SO4)
6. 6
   기타evaporated under reduced pressure
7. 7
   기타to afford a white residue which
8. 8
   기타was recrystallized from acetone-ethanol (5:1)

실험 절차

To a stirred suspension 2 g. of lithium aluminum hydride (LAH) in 250 mL of tetrahydrofuran (THF) was added a slurry of 1 g. (0.003 mole) of 13-amino-6,7,8,9,10,11-hexahydro-3-hydroxy-5-methyl-5,11-methanobenzocyclodecen-12(5H)-one hydrochloride dihydrate in 50 mL of THF over a period of 1 hour. The reaction mixture was refluxed for 25 hours and then cooled and excess LAH was decomposed by careful addition of 2 mL of water. The reaction mixture was filtered and the filtrate washed with aqueous ammonium chloride, dried (anhydrous Na2SO4) and evaporated under reduced pressure to afford a white residue which was recrystallized from acetone-ethanol (5:1) to afford 500 mg (68% yield) of the title compound, mp 232°-235° C.

출처